Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
  • C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
  • C07C271/06—Esters of carbamic acids
  • C07C271/32—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
  • C07C271/36—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
  • C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
  • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
  • C07D471/08—Bridged systems
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
  • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
  • Y02P20/00—Technologies relating to chemical industry
  • Y02P20/50—Improvements relating to the production of bulk chemicals
  • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Definitions

• the AstraZeneca platelet aggregation inhibiting compounds S,3R,4R)-3- hydroxy-4-[7-[(1 S * ,2R * )-2-phenylcyclopropylamino]-5-(propylsulfanyl)-3H-[1 ,2,3] triazolo[4,5-d]pyrimidin-3-yl]cyclopentanecarboxylic acid (11 ) and (1 S,3R,4R)-3-[7- (hexylamino)-5-(propylsulfanyl)-3H-[1 ,2,3]triazolo[4,5-d]pyrimidin-3-yl]-4-hydroxy cyclopentane carboxylic acid (12) taught in Pairaudeau (US Patent 6,166,022) and shown below, could be made by Baeyer-Villiger oxidation of aldehyde 8 with retention of configuration, followed by elaboration of the nitrogen atom on the cyclopentane ring of
• Molecules that contain a functionalized cyclopentane which could be derived from aldehyde 2 or its -Boc derivative 5 ma be found in Blumenkopf et al. WO 99/65908 A1 , Sharma et al, US 2010/0081713 A1 , Johansen et al. WO 2008/033466 A2, Chand et al. WO 2001/000558 A1 , Babu et al. WO 99/33781 A1 , and Babu et al. WO 97/47194 A1 .
• Molecules that contain a functionalized cyclopentane which could be derived from aldehyde 3 or its -Boc derivative 6 may be found in Tibotec WO 2007/014924, Medivir WO 2008/1 19773, WO 1997/025316, Wishart et al. WO 2009/152133 A1 , Kvarnstroem et al. WO 2008/1 19773 A1 , Boehringer et al. WO 2006/048152 A2, and De Haen et al. WO 2001/064708 A1 .
• the beta-secretase 1 (BACE1) inhibitor N1 -benzyl-N2-[6-(3,5- difluorophenoxy)-4(S)-hydroxy-2(R)-methoxy-5(S)-[(1 R,2R,4S)-4-[N-methyl-N- (methylsulfonyl)amino]-2-[N-[1 (S)-phenylethyl]carbamoyl]cyclopentylcarboxamido] hexanoyl]-L-valinamide, reported by Medivir for the treatment of Alzheimer's Dementia (see WO 2008/1 19773), is based on a core cyclopentyl fragment which is introduced using the orthogonally protected amino diacid shown below. This diacid could be readily accessible via oxidation of the correct stereoisomer of aldehyde 3 or its -Boc protected derivative 6, followed by t-butyl ester formation and ring opening via methanolysis.
• HCV NS3 NS4A protease inhibitor N- [(2 R,3aR, 11 aS , 12aR, 14aR)-5-methyl-4 , 14-dioxo-2-(5-phenyl-2H-tetrazol-2-yl)- 1 ,2,3,3a, 4,5,6,7,8,9,1 1 a,12, 12a, 13,14, 14a-hexadecahydrocyclopenta[c]cyclo propa[g][1 ,6]diazacyclotetradecin-12a-ylcarbonyl]cyclopropanesulfonamide, reported by Tibotec in WO 2007/014924 for the treatment of Hepatitis C, is also based on a cyclopentyl fragment that could be accessed from the aldehydes described herein. Oxidation, ester formation, and methanolysis ring opening would once again provide an orthogonally protected synthon suitable for downstream
• Neuraminidase (Sialidase) inhibitor (1 R,3R,4R)-3-[1 (S)-acetamido-2- ethylbutyl]-4-guanidinocyclopentanecarboxylic acid, reported by Biocryst for the treatment of influenza (US 6,562,861 ) could be prepared from the regioisomeric - Boc protected aldehyde 5 also accessible via the route described herein. A Strecker reaction followed by ring opening could furnish the amino acid shown below, which would then allow access to the intermediate cyclopentyl derivative as described.
• the application provides a method of preparing (1 R,4R,6R)- 3-oxo-2-azabicyclo[2.2.1 ]heptane-6-carbaldehyde (2) and (1 S,4S,5S)-3-oxo-2- azabicyclo[2.2.1 ]heptane-5-carbaldehyde (3) :
• the application provides the compounds (1 R,4R,6R)-3-oxo- 2-azabicyclo[2.2.1 ]heptane-6-carbaldehyde (2) and (1 S,4S,5S)-3-oxo-2- azab icyclo[2.2.1 ]heptane-5-carbaldehyde (3) :
• the application provides the compounds (1 R,4R,6R)-ieAt- butyl 6-formyl-3-oxo-2-azabicyclo[2.2.1 ]heptane-2-carboxylate (5) and (1 S,4S,5S)- ie -butyl 5-formyl-3-oxo-2-azabicyclo[2.2.1 ]heptane-2-carboxylate (6):
• the application provides the compound te/f-butyl ((1 R,2R,4R)-2,4-bis(hydroxymethyl)cyclopentyl)carbamate (7):
• the application provides the compound (1 R,3R,4R)-methyl 3-((feri-butoxycarbonyl)amino)-4-formylcyclopentanecarboxylate (8):
• the application provides the compound (1 R,4R,6S)-te/?-butyl 6-(((4 methoxyphenyl)amino)methyl)-3-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate
• the application provides a method of preparing (1 R,4R,6R)- 3-oxo-2-azabicyclo[2.2.1]heptane-6-carbaldehyde (2) and (1 S,4S,5S)-3-oxo-2- azabicyclo[2.2.1 ]heptane-5-carbaldehyde (3):
• the application provides a method of preparing (1 R,4R,6R)- terf-butyl 6-formyl-3-oxo-2-azabicyclo[2.2.1 ]heptane-2-carboxylate (5) and (1 S,4S,5S)-ferf-butyl 5-formyl-3-oxo-2-azabicyclo[2.2.1 ]heptane-2-carboxylate (6):
• the application further comprises the step of reduction of (1 R,4R,6R)-tert-butyl 6-formyl-3-oxo-2-azabicyclo[2.2.1 ]heptane-2-carboxylate (5) to give terf-butyl ((1 R,2R,4R)-2,4-bis(hydroxymethyl)cyclopentyl)carbamate (7).
• the application further comprises the step of methanolysis of (1 R,4R,6R)-tert-butyl 6-formyl-3-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate (5) to give (1 R,3R,4R)-methyl 3-((te/t-butoxycarbonyl)amino)-4-formylcyclopentane carboxylate (8).
• the application further comprises the step of reductive amination of (1 R,4R,6R)-terf-butyl 6-formyl-3-oxo-2-azabicyclo[2.2.1 ]heptane-2- carboxylate (5) to give (1 R,4R,6S)-terf-butyl 6-(((4-methoxyphenyl)amino)methyl) - 3-oxo-2-azabicyclo[2.2.1 ]heptane-2-carboxylate (20).
• the application provides a method of preparing protected (1 R,4R,6R)-6-formyl-3-oxo-2-azabicyclo[2.2.1]heptane (15) and protected (1 S,4S,5S)-butyl 5-formyl-3-oxo-2-azabicyclo[2.2.1 ]heptane (16):
• the application provides a method of preparing (1 R,4R,5R)- 3-oxo-2-azabicyclo[2.2.1 ]heptane-5-carbaldehyde (18) and (1 S,4S,6S)-3-oxo-2- azabicyclo[2.2.1 ]heptane-6-carbaldehyde (19):
• Aldehyde 8 has also been synthesized via basic methanolysis of 5 and has been crystallized to give the desired product in >30:1 yield as shown in Scheme 4.
• Scheme 5
• Alcohol 13 formed by reaction of 2 with sodium borohydride, has been isolated in 26 % yield as a single diastereomer after recrystallization as shown in Scheme 7.
• the number of carbon atoms present in a given group is designated “C x -C y ", where x and y are the lower and upper limits, respectively.
• a group designated as “Cr C 6 " contains from 1 to 6 carbon atoms.
• the carbon number as used in the definitions herein refers to carbon backbone and carbon branching, but does not include carbon atoms of the substituents, such as alkoxy substitutions and the like.
• acac is acetyl acetone or 2,4-pentanedione
• Biphephos is 6,6'-[(3,3'-di- feri-butyl-S.S'-dimethoxy-I '-biphenyl ⁇ '-diy bisioxy ⁇ bisidibenzotdflCl .a ⁇ ] dioxaphosphepin)
• Boc is the tertiary-butyloxycarbonyl group
• DiazaPhos-SPE is 2,2',2",2"'-(1 ,2-phenylenebis [tetrahydro-5,8-dioxo-1 H-[1 ,2,4]diazaphospholo[1 ,2- a]pyridazine-2,1 ,3(3H)-triyl])tetrakis(N-[1 -phenylethyl])benzamide
• D dioxaphosphepin
• Syn gas or synthesis gas
• THF tetrahydrofuran
• TLC thin-layer chromatography
• TMS 2 -HMOB 2,10-di-reri-butyl-6-((5,5'-di-te/ -butyl-2'-((8- methoxy-4H-benzo[d][1 ,3,2]dioxaphosphinin-2-yl)oxy)-3,3'-bis(trimethylsilyl)-[1 ,1 '- biphenyl]-2-yl)oxy)-4,8-bis(trimethylsilyl)dibenzo[d,f][1 ,3,2]dioxaphosphepine
• Tol-BINAP is 2,2'-bis(di-p-tolylphosphino)-1 ,1 '-binaphthyl.
• Amine-protecting group refers to a radical when attached to a nitrogen atom in a target molecule is capable of surviving subsequent chemical reactions applied to the target molecule i.e. hydrogenation, reaction with acylating agents, alkylation etc. The amine-protecting group can later be removed.
• Amine protecting groups include, but are not limited to, fluorenylmethoxycarbonyl (FMOC), terf-butoxycarbonyl (t-BOC), benzyloxycarbonyl (Z), those of the acyl type ⁇ e.g., formyl, benzoyl, trifluoroacetyl, p-tosyl, aryl- and alkylphosphoryl, phenyl- and benzylsulfonyl, o-nitrophenylsulfenyl, o-nitrophenoxyacetyl), and of the urethane type (e.g.
• Amine- protecting groups are made using a reactive agent capable of transferring an amine-protecting group to a nitrogen atom in the target molecule.
• an amine-protecting agent examples include, but are not limited to, C-i-C 6 aliphatic acid chlorides or anhydrides, C 6 -Ci arylcarboxylic acid chlorides or anhydrides, t-butyl chloroformate, di-teri-butyl dicarbonate, butoxycarbonyloxyimino-2- phenylacetonitrile, t-butoxycarbonyl azide, t-butyl fluoroformate, fluorenylmethoxy carbonyl chloride, fluorenylmethoxycarbonyl azide, fluorenylmethoxycarbonyl benzotriazol-1 -yl, (9-fluorenylmethoxycarbonyl)succinimidyl carbonate, fluorenyl methoxycarbonyl pentafluorophexoxide, trichloroacetyl chloride, methyl-, ethyl-, trichloromethyl- chloroformate, and other
• Bosinehydride refers to a reagent containing a B-H group, which is capable of delivering the hydride group to a carbonyl functional group.
• borohydride reagents include, but are not limited to, lithium borohydride, sodium borohydride, potassium borohydride, magnesium borohydride, calcium borohydride, zinc borohydride, triacetoxy sodium borohydride, or sodium cyano borohydride.
• Peracid refers to a reagent containing a -C0 3 H group.
• peracid reagents include, but are not limited to, peracetic acid, propaneperoxoic acid, peroxybenzoic acid, m-chloroperbenzoic acid, peroxytrifluoroacetic acid, performic acid, peroxymaleic acid, or peroxydichloromaleic acid.
• Example 1 (1 ?,4 ?,6fl)-3-oxo-2-azabicyclo[2.2.1]heptane-6- carbaldehyde (2).
• Rh(acac)(CO) 2 (1 mg, 0.4 mol%) in toluene (1 ml_).
• Three pump-purge cycles were carried out using CO:H 2 , the mixture placed under 5 bar of CO:H 2 (1 :1 ), heated to 50 °C in an oil bath and stirred at 1000 rpm with a magnetic cross stirrer bar for 1 hour.
• the autoclave was subsequently removed from the heating bath, depressurized and a solution containing the unsaturated 1 (109 mg, 1 mmol) and tetraethyl silane (30 ⁇ _, 33 mol %) as internal standard in toluene (2 ml_) was injected into the autoclave.
• the autoclave was then pressurized to 4.5 bar CO:H 2 (1 :1 ) heated to 50 °C and stirred at 1000 rpm with a magnetic cross stirrer bar for 90 minutes. The autoclave was then removed from heating, allowed to cool to room temperature and depressurized. Solvent was removed from the crude reaction mixture and the product isolated by column chromatography with ethyl acetate as eluent, the product was isolated as (97% conversion to aldehydes by 1 H NMR spectroscopy based on internal standard, regio-isomeric ratio of 6.3:1 , the major product isomer being 2). Yield: 76 mg (colorless oil), 0.55 mmol (55%).
• Example 2 (1 R,4R,6R)-tert-buty ⁇ 6-formyl-3-oxo-2-azabicyclo[2.2.1 ] heptane-2-carboxylate (5).
• To an oven-dried glass liner of a 300 ml_ autoclave was added (fl,fl)-Kelliphite (17 mg, 0.025 mol%) and Rh(acac)(CO) 2 (3.7 mg, 0.02 mol%).
• Three pump-purge cycles were then carried out using CO:H 2 (1 :1 ), dry toluene (20 ml_) added and the solution placed under 5 bar CO:H 2 (1 : 1 ).
• the autoclave was then heated to 50 °C using an electric heating jacket and stirred at 1000 rpm with an overhead stirrer for 40 minutes.
• the autoclave was
• NOESY and crystal structure confirm exo epimer formed exclusively 2D-NMR used to determine the identity of regioisomer (COSY, HMBC, HSQC).
• Example 3 (1 /?,4/?,6fl)-ferf-Butyl 6-formyl-3-oxo-2-azabicyclo[2.2.1] heptane-2-carboxylate (5).
• the reaction was performed in a 300 ml Parr pressure vessel fitted with a glass liner, double impeller, injection port, bursting disk, pressure relief valve, and pressure gauge.
• the glass liner was charged with Rh(CO) 2 (acac) (3.6 mg, 0.0142 mmol) and (f?,ft)-Kelliphite (16.8 mg, 0.0176 mmol), the vessel sealed and flushed three times with nitrogen (145 psi).
• Toluene (20 ml, anhydrous, and deoxygenated) was added to the vessel via the injection port and the system flushed three times with Syn gas (145 psi, 1 :1 ).
• the vessel was heated to 50 °C, charged to 90 psi with Syn gas (1 :1 ) and stirred (1 ,000 rpm) for 40 minutes. After this time, the stirring was stopped and the pressure released.
• a toluene solution (40 ml, anhydrous and deoxygenated) of /V-Boc-(-)- lactam (4, 15.0 g, 21 mmol) was then added via syringe and the vessel flushed a further three times with Syn gas (145 psi, 1 :1).
• the reaction was stirred (1000 rpm), heated to 50 °C, and charged to 65 psi with Syn gas (1 :1 ). The pressure was monitored and maintained at this pressure for 16 hours. The stirring was reduced to 500 rpm and the vessel allowed to cool to room temperature, vented to atmosphere, flushed once with nitrogen (145 psi) and opened. An aliquot of the reaction mixture was analyzed by 1 H NMR spectroscopy, showing the reaction had gone to completion with a ratio of 7.1 :1 in favor of the exo-aldehyde ⁇ to the NH. The reaction mixture was reduced to dryness and dissolved in toluene (20 mL). This was placed in the freezer for one week to aid crystallization, after which time filtration yielded 9.3 g of crystalline material (58 % yield, ⁇ : ⁇ 17.5:1 ).
• Example 4 (1 S,4S,5S)-ferf-Butyl 5-formyl-3-oxo-2-azabicyclo[2.2.1 ] heptane-2-carboxylate (6).
• a catalyst solution containing (S,S)-Kelliphite 4.8 mg, 0.5 mol%) and Rh(acac)(CO)2 (1 mg, 0.4 mol%) in toluene (1 mL).
• Three pump-purge cycles were carried out using CO:H 2 and the mixture placed under 5 bar CO:H 2 (1 :1 ), heated to 50 °C in an oil bath and stirred at 1000 rpm with a magnetic cross stirrer bar for 40 minutes.
• the autoclave was subsequently removed from the heating bath, cooled to room temperature, depressurized and a solution containing 4 (209 mg, 1 mmol) and tetraethyl silane (30 ⁇ _, 33 mol%) as internal standard in toluene (2 ml_) was injected into the autoclave.
• the autoclave was then pressurized with 4.5 bar CO:H 2 (1 :1 ) and stirred at 1000 rpm with a magnetic cross stirrer bar at room temperature for 15 hours.
• the autoclave was then removed from heating, allowed to cool to room temperature and depressurized.
• Example 5 (1 /?,4fl,6 3 ⁇ 4-6-(Hydroxymethyl)-2azabicyclo[2.2.1]heptan-3- one (13). Solvent was removed under reduced pressure from a crude asymmetric hydroformylation reaction (358 mg, 2.58 mmol of substrate) and the resulting residue dissolved in ethanol (15 ml_). To this solution was then added sodium borohydride (98 mg, 1 eq.) and the reaction mixture stirred for 4 hours, upon which time no starting material remained by TLC analysis. Acetone was then added and the reaction allowed to stir for 5 minutes. Hydrochloric acid (0.1 M) was then added to pH neutral and the water removed under reduced pressure.
• Example 8 (1 /7,3/?,4fl)-Methyl 3-((fert-butoxycarbonyl)amino)-4-formyl cyclopentane carboxylate (8).
• Aldehyde 5 (880 mg, 3.68 mmol, > 28:1 regio- isomeric ratio) was dissolved in methanol (10 mL) and placed under a nitrogen atmosphere. The reaction mixture was then cooled to 0 °C, sodium methoxide (219 mg, 4.06 mmol, 1.1 eq.) was added, and the reaction allowed to stir for 10 minutes at 0°C. The reaction vessel was then allowed to warm to room
• Example 9 (1 S,4S,5S)-3-Oxo-2-azabicyclo[2.2.1]heptane-5-carb aldehyde (3).
• (S,S)-Kelliphite as modifying ligand the other regio-isomer, 3 was formed in excess (up to 7.15:1 ).
• NOESY confirms exo-epimer formed exclusively.
• 2D-NMR spectroscopy used to determine identity of regioisomer (COSY, HMBC, and HSQC).
• Example 10 (1 /?,4S)-ferf-Butyl 3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2- carboxylate (4). The product was purified by recrystallization from boiling hexane to leave a pale orange solid.
• Example 11 (1 H,4/?,6 ?)-iert-Butyl 6-formyl-3-oxo-2-azabicyclo[2.2.1] heptane-2-carboxylate (5).
• To an oven-dried glass liner of a 300 ml_ autoclave was added (/?,f?)-Kelliphite (17 mg, 0.025 mol%) and [Rh(acac)(CO) 2 ] (3.7 mg, 0.02 mol%).
• Three pump-purge cycles were then carried out using CO:H 2 (1 :1 ), dry toluene (20 ml_) added and the solution placed under 5 bar CO: H2 (1 :1).
• the autoclave was then heated to 50 °C using an electric heating jacket and stirred at 1000 rpm with an overhead stirrer for 40 minutes.
• the autoclave was
• Example 12 (1 S,4S,5S)-fert-Butyl 5-formyl-3-oxo-2-azabicyclo[2.2.1] heptane-2-carboxylate (6). To a 50 mL autoclave (pre-purged with nitrogen gas) was added a catalyst solution containing (S,S)-Kelliphite (4.8 mg, 0.5 mol%) and [Rh(acac)(CO) 2 ] (1 mg, 0.4 mol%) in toluene (1 mL).
• Example 13 (1 H,4H,6/?)-6-(Hydroxymethyl)-2-azabicyclo[2.2.1]heptan- 3-one (13).
• the solvent was removed under reduced pressure from a crude asymmetric hydroformylation reaction (358 mg, 2.58 mmol of substrate) and the resulting residue dissolved in ethanol (15 mL).
• sodium borohydride 98 mg, 2.58 mmol, 1 eq.
• Acetone was then added and the reaction allowed to stir for 5 minutes.
• Hydrochloric acid (0.1 M) was added to pH neutral and the water was removed under reduced pressure.
• CD 3 OD) 6 C 184.2 (C3), 64.0 (C8), 56.9 (C1 ), 46.3 (C6), 44.8 (C4), 38.1 (C7), 27.4 (C5);
• the structure depicted for the compounds within the present application are also meant to include all isomeric (e.g., enantiomeric or conformational) forms of the structures.
• isomeric e.g., enantiomeric or conformational
• both the R and the S configurations at the stereogenic carbon are included in this application. Therefore, single stereochemical isomers as well as enantiomeric and conformational mixtures of the present compound are within the scope of the application.
• It is well known in the art how to prepare optically active forms, such as by resolution of racemic forms or by synthesis from optically active starting materials.
• structures depicted here are also meant to include compounds that differ only in the presence of one or more isotopically enriched atoms.

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