Benzylamine → Ethyl (1R,2R,3S,6S)-6-[(benzylamino)methyl]-3-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-2-(4-fluorophenyl)cyclohexanecarboxylate

HRID 2245249노트

반응식

HRID 2245249 반응식
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@H:16]2[CH2:21][CH2:20][C@H:19]([CH:22]=O)[C@@H:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C@@H:17]2[C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH2:38]([NH2:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:38]([NH:45][CH2:22][C@@H:19]1[C@@H:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C@H:17]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[C@@H:16]([O:15][C@@H:13]([C:5]2[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=[C:3]([C:2]([F:37])([F:36])[F:1])[CH:4]=2)[CH3:14])[CH2:21][CH2:20]1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

참가 물질

5

반응물 3

HCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86628113Ethyl(1S,2R,3S,6S)-3-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-2-(4-fluorophenyl)-6-formylcyclohexanecarboxylate

생성물 1

HCID 86628114Ethyl (1R,2R,3S,6S)-6-[(benzylamino)methyl]-3-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-2-(4-fluorophenyl)cyclohexanecarboxylate수율 97%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of aldehyde obtained from Step C (0.45 g, 0.84 mmol), benzyl amine (0.093 mL, 0.85 mmol), sodium triacetoxy borohydride (0.55 g, 2.6 mmol) in 30 mL dichloromethane was stirred at room temperature for 12 hr. The reaction mixture was washed with 2 N aq. NaOH, brine, dried over MgSO4, filtered and the solvent was removed under vacuum to give the title compound (0.51 g) which was used without further purification. MS: (MH)+ 626.6.

후처리

  1. washThe reaction mixture was washed with 2 N aq. NaOH, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customthe solvent was removed under vacuum

출처 및 근거

ORD 기록
ord-d2ebb5741dc04750a3703540432101cc
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07683068B2

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