GB1460781A - Hydrogen transfer process - Google Patents
Hydrogen transfer processInfo
- Publication number
- GB1460781A GB1460781A GB1578174A GB1578174A GB1460781A GB 1460781 A GB1460781 A GB 1460781A GB 1578174 A GB1578174 A GB 1578174A GB 1578174 A GB1578174 A GB 1578174A GB 1460781 A GB1460781 A GB 1460781A
- Authority
- GB
- United Kingdom
- Prior art keywords
- optically active
- polyiminoalane
- alane
- butylamine
- proviso
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000001257 hydrogen Substances 0.000 title abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 title abstract 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- 229910000086 alane Inorganic materials 0.000 abstract 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 abstract 1
- CWKYHZMWPLSOFA-UHFFFAOYSA-N 3-methyl-1-phenyl-2,5-dihydrophosphole Chemical compound C1C(C)=CCP1C1=CC=CC=C1 CWKYHZMWPLSOFA-UHFFFAOYSA-N 0.000 abstract 1
- ZFAGOADKDXXTSV-UHFFFAOYSA-N 3-methylpentan-2-amine Chemical compound CCC(C)C(C)N ZFAGOADKDXXTSV-UHFFFAOYSA-N 0.000 abstract 1
- 229910018509 Al—N Inorganic materials 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N alpha-methylbenzylalcohol Natural products CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000000460 chlorine Chemical group 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/52—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of imines or imino-ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/069—Aluminium compounds without C-aluminium linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/505—Preparation; Separation; Purification; Stabilisation
- C07F9/509—Preparation; Separation; Purification; Stabilisation by reduction of pentavalent phosphorus derivatives, e.g. -P=X with X = O, S, Se or -P-Hal2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
1460781 Reduction SNAMPROGETTI SpA 9 April 1974 [13 April 1973] 15781/74 Headings C2C and C2P The invention comprises a process for converting by hydrogen transfer a prochiral or racemic starting material to an optically active product, which process comprises reacting the starting material with an alane selected from (a) optically active aminoalanes having the two following general formulae and and (b) optically active polyiminoalanes having in their molecule a group having the general formula wherein X is a hydrogen, chlorine or bromine atom or a group of the formula -NR<SP>3</SP> 2 or -OR<SP>3</SP>, n is an integer having a value greater than 4, each of R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP>, which can be the same or different, is an alkyl, aryl, alkaryl, aralkyl or cycloalkyl radical, or R<SP>1</SP> and R<SP>2</SP> together represent a divalent alkylene radical and with the nitrogen atom to which they are attached form a hetero ring; with the proviso that in the alane at least one radical attached to the nitrogen atom(s) contains at least one asymmetric centre, and with the proviso that in the polyiminoalane there is for each aluminium atom, at least one direct Al-N bond and in the polyiminoalane there is at least one Al-H bond. Examples describe the preparation of α- methyl benzyl alcohol; but-2-yl-n-butylamine; 3 - methyl - 1 - phenyl - 1 - phosphacyclopent- 3-ene and 1,2-dimethyl-n-butylamine.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT22954/73A IT987071B (en) | 1973-04-13 | 1973-04-13 | ASYMMETRIC HYDROGENATION BY MEANS OF OPTICALLY ACTS VI DERIVATIVES OF ALUMINUM HYDRORO |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1460781A true GB1460781A (en) | 1977-01-06 |
Family
ID=11202251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1578174A Expired GB1460781A (en) | 1973-04-13 | 1974-04-09 | Hydrogen transfer process |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5929045B2 (en) |
| BE (1) | BE813718A (en) |
| CA (1) | CA1021801A (en) |
| CH (1) | CH606032A5 (en) |
| CS (1) | CS203074B2 (en) |
| DD (1) | DD113740A5 (en) |
| DK (1) | DK137922B (en) |
| FR (1) | FR2225397B1 (en) |
| GB (1) | GB1460781A (en) |
| HU (1) | HU176607B (en) |
| IT (1) | IT987071B (en) |
| LU (1) | LU69850A1 (en) |
| NL (1) | NL7404845A (en) |
| NO (1) | NO142864C (en) |
| SE (1) | SE419550B (en) |
| YU (1) | YU96574A (en) |
| ZA (1) | ZA742324B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006079819A2 (en) * | 2005-01-27 | 2006-08-03 | University Of Nottingham | Improved method for the preparation of enantiomerically enriched secondary alcohols by the addition of organoaluminium reagents to carbonyl compounds |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2714721A1 (en) * | 1976-05-17 | 1977-12-01 | Texas Alkyls Inc | REDUCTION OF TRIPHENYLPHOSPHINE OXIDE TO TRIPHENYLPHOSPHINE |
| US5189208A (en) * | 1991-07-01 | 1993-02-23 | Ethyl Corporation | Ibuprofen resolution |
-
1973
- 1973-04-13 IT IT22954/73A patent/IT987071B/en active
-
1974
- 1974-04-04 NO NO741246A patent/NO142864C/en unknown
- 1974-04-08 YU YU00965/74A patent/YU96574A/en unknown
- 1974-04-08 CH CH487074A patent/CH606032A5/xx not_active IP Right Cessation
- 1974-04-09 NL NL7404845A patent/NL7404845A/xx active Search and Examination
- 1974-04-09 GB GB1578174A patent/GB1460781A/en not_active Expired
- 1974-04-10 ZA ZA00742324A patent/ZA742324B/en unknown
- 1974-04-10 SE SE7404949A patent/SE419550B/en not_active IP Right Cessation
- 1974-04-10 DK DK202374AA patent/DK137922B/en not_active IP Right Cessation
- 1974-04-10 FR FR7412543A patent/FR2225397B1/fr not_active Expired
- 1974-04-11 DD DD177852A patent/DD113740A5/xx unknown
- 1974-04-11 CA CA197,532A patent/CA1021801A/en not_active Expired
- 1974-04-12 CS CS742668A patent/CS203074B2/en unknown
- 1974-04-12 JP JP49040466A patent/JPS5929045B2/en not_active Expired
- 1974-04-12 BE BE143208A patent/BE813718A/en not_active IP Right Cessation
- 1974-04-12 HU HU74SA2625A patent/HU176607B/en unknown
- 1974-04-12 LU LU69850A patent/LU69850A1/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006079819A2 (en) * | 2005-01-27 | 2006-08-03 | University Of Nottingham | Improved method for the preparation of enantiomerically enriched secondary alcohols by the addition of organoaluminium reagents to carbonyl compounds |
| WO2006079819A3 (en) * | 2005-01-27 | 2007-05-10 | Univ Nottingham | Improved method for the preparation of enantiomerically enriched secondary alcohols by the addition of organoaluminium reagents to carbonyl compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| NO142864C (en) | 1980-11-05 |
| NL7404845A (en) | 1974-10-15 |
| IT987071B (en) | 1975-02-20 |
| DK137922C (en) | 1978-10-30 |
| DE2416396A1 (en) | 1974-10-31 |
| CH606032A5 (en) | 1978-10-13 |
| JPS5076002A (en) | 1975-06-21 |
| NO142864B (en) | 1980-07-28 |
| NO741246L (en) | 1974-10-15 |
| HU176607B (en) | 1981-03-28 |
| DK137922B (en) | 1978-06-05 |
| AU6753874A (en) | 1975-10-09 |
| ZA742324B (en) | 1975-04-30 |
| FR2225397A1 (en) | 1974-11-08 |
| CS203074B2 (en) | 1981-02-27 |
| SE419550B (en) | 1981-08-10 |
| JPS5929045B2 (en) | 1984-07-18 |
| LU69850A1 (en) | 1974-07-18 |
| DE2416396B2 (en) | 1977-02-17 |
| CA1021801A (en) | 1977-11-29 |
| DD113740A5 (en) | 1975-06-20 |
| FR2225397B1 (en) | 1976-06-25 |
| BE813718A (en) | 1974-07-31 |
| YU96574A (en) | 1982-05-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |