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

HRID 2245249ノート

反応式

HRID 2245249 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d2ebb5741dc04750a3703540432101cc
出典データセット
uspto-grants-2010_03
特許番号
US07683068B2

反応ノート

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