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

HRID 2245249Notes

Reaction equation

HRID 2245249 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d2ebb5741dc04750a3703540432101cc
Source dataset
uspto-grants-2010_03
Patent number
US07683068B2

Reaction notes

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