JP5902575B2 - 光学活性含フッ素アミン化合物の製造方法並びに光学活性含フッ素アミン化合物 - Google Patents
光学活性含フッ素アミン化合物の製造方法並びに光学活性含フッ素アミン化合物 Download PDFInfo
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- JP5902575B2 JP5902575B2 JP2012161056A JP2012161056A JP5902575B2 JP 5902575 B2 JP5902575 B2 JP 5902575B2 JP 2012161056 A JP2012161056 A JP 2012161056A JP 2012161056 A JP2012161056 A JP 2012161056A JP 5902575 B2 JP5902575 B2 JP 5902575B2
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- Prior art keywords
- trifluoro
- amino
- propane
- group
- iodide
- 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.)
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- -1 amine compound Chemical class 0.000 title claims description 32
- 238000000034 method Methods 0.000 title description 10
- 238000004519 manufacturing process Methods 0.000 claims description 16
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 239000011737 fluorine Substances 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 6
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 17
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000001294 propane Substances 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- NHXPOSUWTYJINF-CYBMUJFWSA-N FC([C@@H](C1CCCCC1)NC(C1=CC=CC=C1)=O)(F)F Chemical compound FC([C@@H](C1CCCCC1)NC(C1=CC=CC=C1)=O)(F)F NHXPOSUWTYJINF-CYBMUJFWSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 3
- 150000001351 alkyl iodides Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- FUCOMWZKWIEKRK-UHFFFAOYSA-N iodocyclohexane Chemical compound IC1CCCCC1 FUCOMWZKWIEKRK-UHFFFAOYSA-N 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- HTJYTQSIEXSPGU-SSDOTTSWSA-N (1r)-1-cyclohexyl-2,2,2-trifluoroethanamine Chemical compound FC(F)(F)[C@H](N)C1CCCCC1 HTJYTQSIEXSPGU-SSDOTTSWSA-N 0.000 description 2
- QBTHFIYAMWNLPG-SECBINFHSA-N (2R)-1,1,1-trifluoro-3-(2-methoxyphenyl)propan-2-amine Chemical compound COC1=CC=CC=C1C[C@H](C(F)(F)F)N QBTHFIYAMWNLPG-SECBINFHSA-N 0.000 description 2
- KCUGSCGBFLYBTO-MRVPVSSYSA-N (2R)-1,1,1-trifluoro-3-[2-(trifluoromethyl)phenyl]propan-2-amine Chemical compound C1=CC=C(C(=C1)C[C@H](C(F)(F)F)N)C(F)(F)F KCUGSCGBFLYBTO-MRVPVSSYSA-N 0.000 description 2
- WADMYCZCPXXMSC-MRVPVSSYSA-N (2R)-1,1,1-trifluoro-3-[4-(trifluoromethyl)phenyl]propan-2-amine Chemical compound C1=CC(=CC=C1C[C@H](C(F)(F)F)N)C(F)(F)F WADMYCZCPXXMSC-MRVPVSSYSA-N 0.000 description 2
- JFHQGVOJXRJISL-ZCFIWIBFSA-N (2R)-1,1,1-trifluoroheptan-2-amine Chemical compound CCCCC[C@@H](N)C(F)(F)F JFHQGVOJXRJISL-ZCFIWIBFSA-N 0.000 description 2
- KIKOUJITKDXNMI-MRVPVSSYSA-N (2R)-3-(3-bromophenyl)-1,1,1-trifluoropropan-2-amine Chemical compound C1=CC(=CC(=C1)Br)C[C@H](C(F)(F)F)N KIKOUJITKDXNMI-MRVPVSSYSA-N 0.000 description 2
- KGESSPWDYQFDTL-MRVPVSSYSA-N (2R)-3-(3-chlorophenyl)-1,1,1-trifluoropropan-2-amine Chemical compound FC([C@@H](CC1=CC(=CC=C1)Cl)N)(F)F KGESSPWDYQFDTL-MRVPVSSYSA-N 0.000 description 2
- NNBKWYLYECKWRH-MRVPVSSYSA-N (2R)-3-(4-bromophenyl)-1,1,1-trifluoropropan-2-amine Chemical compound C1=CC(=CC=C1C[C@H](C(F)(F)F)N)Br NNBKWYLYECKWRH-MRVPVSSYSA-N 0.000 description 2
- QBTHFIYAMWNLPG-VIFPVBQESA-N (2S)-1,1,1-trifluoro-3-(2-methoxyphenyl)propan-2-amine Chemical compound COC1=CC=CC=C1C[C@@H](C(F)(F)F)N QBTHFIYAMWNLPG-VIFPVBQESA-N 0.000 description 2
- KCUGSCGBFLYBTO-QMMMGPOBSA-N (2S)-1,1,1-trifluoro-3-[2-(trifluoromethyl)phenyl]propan-2-amine Chemical compound C1=CC=C(C(=C1)C[C@@H](C(F)(F)F)N)C(F)(F)F KCUGSCGBFLYBTO-QMMMGPOBSA-N 0.000 description 2
- WADMYCZCPXXMSC-QMMMGPOBSA-N (2S)-1,1,1-trifluoro-3-[4-(trifluoromethyl)phenyl]propan-2-amine Chemical compound C1=CC(=CC=C1C[C@@H](C(F)(F)F)N)C(F)(F)F WADMYCZCPXXMSC-QMMMGPOBSA-N 0.000 description 2
- KIKOUJITKDXNMI-QMMMGPOBSA-N (2S)-3-(3-bromophenyl)-1,1,1-trifluoropropan-2-amine Chemical compound C1=CC(=CC(=C1)Br)C[C@@H](C(F)(F)F)N KIKOUJITKDXNMI-QMMMGPOBSA-N 0.000 description 2
- KGESSPWDYQFDTL-QMMMGPOBSA-N (2S)-3-(3-chlorophenyl)-1,1,1-trifluoropropan-2-amine Chemical compound FC([C@H](CC1=CC(=CC=C1)Cl)N)(F)F KGESSPWDYQFDTL-QMMMGPOBSA-N 0.000 description 2
- NNBKWYLYECKWRH-QMMMGPOBSA-N (2S)-3-(4-bromophenyl)-1,1,1-trifluoropropan-2-amine Chemical compound C1=CC(=CC=C1C[C@@H](C(F)(F)F)N)Br NNBKWYLYECKWRH-QMMMGPOBSA-N 0.000 description 2
- OBMZKLDWSOWUMC-MRVPVSSYSA-N (2r)-3-(4-chlorophenyl)-1,1,1-trifluoropropan-2-amine Chemical compound FC(F)(F)[C@H](N)CC1=CC=C(Cl)C=C1 OBMZKLDWSOWUMC-MRVPVSSYSA-N 0.000 description 2
- OBMZKLDWSOWUMC-QMMMGPOBSA-N (2s)-3-(4-chlorophenyl)-1,1,1-trifluoropropan-2-amine Chemical compound FC(F)(F)[C@@H](N)CC1=CC=C(Cl)C=C1 OBMZKLDWSOWUMC-QMMMGPOBSA-N 0.000 description 2
- ROENHWPLAVWLHX-UHFFFAOYSA-N 1-(1-fluorocyclohexyl)ethanamine Chemical compound CC(N)C1(F)CCCCC1 ROENHWPLAVWLHX-UHFFFAOYSA-N 0.000 description 2
- ZINKVTDSTRINMX-UHFFFAOYSA-N 1-fluoro-3-[3-(trifluoromethyl)phenyl]propan-2-amine Chemical compound FCC(CC1=CC(=CC=C1)C(F)(F)F)N ZINKVTDSTRINMX-UHFFFAOYSA-N 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- ZYQSFYKAFMOHIJ-QMMMGPOBSA-N C1=CC=C(C(=C1)C[C@@H](C(F)(F)F)N)F Chemical compound C1=CC=C(C(=C1)C[C@@H](C(F)(F)F)N)F ZYQSFYKAFMOHIJ-QMMMGPOBSA-N 0.000 description 2
- ZYQSFYKAFMOHIJ-MRVPVSSYSA-N C1=CC=C(C(=C1)C[C@H](C(F)(F)F)N)F Chemical compound C1=CC=C(C(=C1)C[C@H](C(F)(F)F)N)F ZYQSFYKAFMOHIJ-MRVPVSSYSA-N 0.000 description 2
- WMMFXUXPYDEXHK-VIFPVBQESA-N CC1=CC(=CC=C1)C[C@@H](C(F)(F)F)N Chemical compound CC1=CC(=CC=C1)C[C@@H](C(F)(F)F)N WMMFXUXPYDEXHK-VIFPVBQESA-N 0.000 description 2
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- MOFUEHKUGUJIJY-VIFPVBQESA-N CC1=CC=CC=C1C[C@@H](C(F)(F)F)N Chemical compound CC1=CC=CC=C1C[C@@H](C(F)(F)F)N MOFUEHKUGUJIJY-VIFPVBQESA-N 0.000 description 2
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- JMKPJVAVQWOIRO-LBPRGKRZSA-N CCCCCCCCCCC[C@@H](C(F)(F)F)N Chemical compound CCCCCCCCCCC[C@@H](C(F)(F)F)N JMKPJVAVQWOIRO-LBPRGKRZSA-N 0.000 description 2
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- KOXTUGDDJZBLKS-QMMMGPOBSA-N FC([C@H](CCCCCCC)N)(F)F Chemical compound FC([C@H](CCCCCCC)N)(F)F KOXTUGDDJZBLKS-QMMMGPOBSA-N 0.000 description 2
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 2
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000007342 radical addition reaction Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
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- ABFFFMOFSKFMBE-SSDOTTSWSA-N (2R)-1,1,1-trifluorooctan-2-amine Chemical compound CCCCCC[C@@H](N)C(F)(F)F ABFFFMOFSKFMBE-SSDOTTSWSA-N 0.000 description 1
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- FGRVOLIFQGXPCT-UHFFFAOYSA-L dipotassium;dioxido-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound [K+].[K+].[O-]S([O-])(=O)=S FGRVOLIFQGXPCT-UHFFFAOYSA-L 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- PCEBAZIVZVIQEO-UHFFFAOYSA-N iodocyclopentane Chemical compound IC1CCCC1 PCEBAZIVZVIQEO-UHFFFAOYSA-N 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- XJTQJERLRPWUGL-UHFFFAOYSA-N iodomethylbenzene Chemical compound ICC1=CC=CC=C1 XJTQJERLRPWUGL-UHFFFAOYSA-N 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N n-heptane Substances CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 150000005527 organic iodine compounds Chemical class 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- CESUXLKAADQNTB-UHFFFAOYSA-N tert-butanesulfinamide Chemical compound CC(C)(C)S(N)=O CESUXLKAADQNTB-UHFFFAOYSA-N 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- SCHZCUMIENIQMY-UHFFFAOYSA-N tris(trimethylsilyl)silicon Chemical compound C[Si](C)(C)[Si]([Si](C)(C)C)[Si](C)(C)C SCHZCUMIENIQMY-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
[項1] 下記式(1)
R1-I (3)
(式中、R1はメチル基、エチル基、炭素数3〜12の直鎖、分岐若しくは環式のアルキル基、フェニル基、置換フェニル基、ベンジル基または置換ベンジル基を示す)
で表される有機ヨウ化物を、ラジカル開始剤存在下及び/または光照射下、かつ還元剤存在下反応させることを特徴とする下記一般式(4)
または下記一般式(5)
で表される光学活性含フッ素アミン化合物の製造方法
で表される光学活性含フッ素アミン化合物、または下記一般式(7)
で表される光学活性含フッ素アミン化合物
を提供するものである。
窒素雰囲気下にて、トリフルオロメチル (R)−tert−ブチルスルフィンイミド(40.2mg,0.2mmol、以下R−F3TBSIと略す)をCH2Cl2(1.5ml)に溶解した。そこにシクロヘキシルアイオダイド(126.0mg,0.6mmol,3.0eq.)、トリストリメチルシリルシラン(0.20 ml,3.0eq.)、CH2Cl2 (0.5ml)に溶解させた2,2’−アゾビス(イソブチロニトリル)6.5 mg(0.2 eq.)を添加し、室温にて高圧水銀ランプによる光照射を6時間行った。反応後、過剰量のヘキサンを添加し、再結晶による精製を行い、目的物の(R)−2,2,2−トリフルオロ−1−シクロヘキシルエチル−1−アミンを得た(31.2mg,0.17mmol,収率86%)。なお光学純度については実施例2の(R)−2,2,2−トリフルオロ−1−ベンゾイルアミノ−1−シクロヘキシルエタンに誘導し98%ee(R)と決定した。
1F−NMR(376MHz,CDCl3)δ−68.65。
13C−NMR(100MHz,CDCl3)δ123.70(q,J=300.5),58.60(q,J=31.2),36.48,29.32,28.50,25.76(d,J=3.6),25.26。
HRMS(ESI+)C8H15NF3[M+H](calcd182.1151,found182.1153)。
実施例1と同じ製法で調製した反応液に塩化ベンゾイル(70 μl, 3.0 eq.)、トリエチルアミン(84 μl, 3.0 eq.)、DMAP(1 piece)を加え、室温で一晩撹拌を行った。反応後1N塩酸を加え、反応を止めた。CH2Cl2で抽出した後、硫酸ナトリウムでろ過し、溶液を濃縮後、カラムクロマトグラフィーによる精製を行うことにより、目的物の(R)−2,2,2−トリフルオロ−1−ベンゾイルアミノ−1−シクロヘキシルエタンを得た(49.1mg,0.17mmol,収率86%)。
1F−NMR(376MHz,CDCl3)δ−71.57。
13C−NMR(100MHz,CDCl3)δ167.43,133.73,132.15,128.81,127.07,125.39(q,J=283.6),54.72(q,J=28.9),37.48,30.04,27.43,25.92,25.79(d,J=6.0)。
HRMS(ESI+)C15H18ONF3Na[M+Na]+(calcd308.1233,found308.1233)。
HRMS(ESI−)C15H17ONF3[M−H](calcd284.1247,found 284.1274)。
実施例1及び実施例2の製法に従い、シクロヘキシルアイオダイドを表1中に示したアルキルアイオダイドに替え、トリフルオロメチル (R)−tert−ブチルスルフィンイミドをトリフルオロメチル (S)−tert−ブチルスルフィンイミド(以下、S−F3TBSIと略す)に替えた以外、実施例1及び実施例2と同じ操作を行い、表1中に示した化合物を得た。結果を表1中に示した。
1H NMR(400MHz,CDCl3)δ7.79(2H,d,J=6.8Hz,Ph),7.55(1H,t,J=8.0Hz,Ph),7.47(2H,t,J=8.0Hz,Ph),6.11(1H,d,J=6.8Hz,NH),4.98−4.92(1H,m,CF3CH),1.44(3H,d,J=13.2Hz,CH3CH)。
19F−NMR(376MHz,CDCl3)δ−77.35。
13C−NMR(100MHz,CDCl3)δ166.91,133.43,132.17,128.77,127.06,125.40(q,J=282.4),46.74 q,J=62.5),14.56。
HRMS(ESI+)C10H10ONF3Na[M+Na]+(calcd240.0607,found240.0612)。
HRMS(ESI−)C10H9ONF3[M−H](calcd216.0631,found216.0637)。
1H−NMR(400MHz,CDCl3)δ7.79(2H,d,J=8.4Hz,Ph),7.53(1H,t,J=7.2Hz,Ph),7.47(2H,t,J=8.0Hz,Ph),6.07(1H,d,J=9.6Hz,NH),4.87−4.78(1H,m,CF3CH),1.94−1.86(1H,m,C5H11),1.64−1.56(1H,m,C5H11),1.45−1.22(6H,m,C5H11),0.88(3H,t,J=5.6Hz,C5H11)。
19F−NMR(376MHz,CDCl3)δ−75.90。
13C−NMR(100MHz,CDCl3)δ167.40,133.50,132.14,128.78,127.07,125.34(q,J=282.4),50.71(q,J=29.4),31.23,28.43,24.81,22.35,13.93。
HRMS(ESI+)C14H18ONF3Na[M+Na]+(calcd296.1232,found296.1231)。
HRMS(ESI−)C14H17ONF3[M−H](calcd272.1257,found272.1267)。
1H−NMR(400MHz,CDCl3)δ7.79(2H,d,J=7.2Hz,Ph),7.54(1H,tt,J=1.2,6.0Hz,Ph),7.47(2H,t,J=8.4Hz,Ph),6.05(1H,d,J=9.2Hz,NH),4.87−4.79(1H,m,CF3CH),1.95−1.86(1H,m,C6H11),1.64−1.55(1H,m,C6H11),1.44−1.26(8H,m,C6H11),0.87(3H,t,J=6.8Hz,C6H11)。
19F−NMR(376MHz,CDCl3)δ−75.87。
13C−NMR(100MHz,CDCl3)δ167.34,133.48,132.11,128.74,127.04,125.28(q,J=349.5),50.70(q,J=37.2),31.47,28.70,25.08,22.47,13.98。
HRMS(ESI+)C15H20ONF3Na[M+Na]+(calcd310.1389,found310.1383)。
HRMS(ESI−)C15H19ONF3[M−H](calcd286.1414,found286.1421)。
1H−NMR(400MHz,CDCl3)δ7.79(2H,d,J=7.2Hz,Ph),7.55(1H,t,J=6.8Hz,Ph),7.47(2H,t,J=7.6Hz,Ph),6.02(1H,d,J=9.2Hz,NH),4.87−4.79(1H,m,CF3CH),1.94−1.86(1H,m,C10H21),1.63−1.54(1H,m,C10H21),1.47−1.24(16H,m,C10H21),0.87(3H,t,J=7.2Hz,C10H21)。
19F−NMR(376MHz,CDCl3)δ−75.87。
13C−NMR(100MHz,CDCl3)δ167.33,133.47,132.11,128.74,127.04,125.32(q,J=250.6),50.55(q,J=38.4),31.85,29.47(d,J=6.0),29.27(d,J=3.5),28.48,25.11,22.65,14.09。
HRMS(ESI+)C19H28ONF3Na[M+Na]+(calcd366.2016,found366.2018)。
HRMS(ESI−)C19H27ONF3[M−H](calcd342.2039,found342.2046)。
1H−NMR(400MHz,CDCl3)δ7.79(2H,d,J=6.8Hz,Ph),7.56(1H,t,J=7.2Hz,Ph),7.48(2H,t,J=6.4Hz,Ph),6.17(1H,d,J=9.2Hz,NH),4.81−4.75(1H,m,CF3CH),2.31−2.21(1H,m,(CH3)2CH),1.06(6H,dd,J=6.8,9.2Hz,(CH3)2CH)。
19F−NMR(376MHz,CDCl3)δ−72.15。
13C−NMR(100MHz,CDCl3)δ167.44,133.58,132.13,128.79,126.99,125.35(q,J=354.3),54.76(q,J=36.0),27.74,19.96,17.11。
HRMS(ESI+)C12H14ONF3Na[M+Na]+(calcd268.0920,found268.0919)。
HRMS(ESI−)C12H13ONF3[M−H](calcd244.0944,found244.0952)。
実施例1のCH2Cl2をベンゼンに替え、高圧水銀灯を用いず油浴上で還流下、反応した以外実施例1と同じ反応操作を行い、目的物の(R)−2,2,2−トリフルオロ−1−シクロヘキシルエチル−1−アミンを得た(収率60%,98%ee(R))。
Claims (1)
- 下記式(1)
で表されるトリフルオロメチル (R)−tert−ブチルスルフィンイミドまたは下記式(2)
で表されるトリフルオロメチル (S)−tert−ブチルスルフィンイミドと下記一般式(3)
R1−I (3)
(式中、R1はメチル基、エチル基、炭素数3〜12の直鎖、分岐若しくは環式のアルキル基、フェニル基、置換フェニル基、ベンジル基または置換ベンジル基を示す)
で表される有機ヨウ化物を、ラジカル開始剤存在下及び/または光照射下、かつ還元剤存在下反応させることを特徴とする下記一般式(4)
(式中のR1は前記に同じ)
または下記一般式(5)
(式中のR1は前記に同じ)
で表される光学活性含フッ素アミン化合物の製造方法。
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