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

HRID 2245250Notes

Reaction equation

HRID 2245250 reaction equation
C([NH:8][CH2:9][C@@H:10]1[C@@H:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C@H:14]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[C@@H:13]([O:28][C@@H:29]([C:31]2[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[C:33]([C:41]([F:44])([F:43])[F:42])[CH:32]=2)[CH3:30])[CH2:12][CH2:11]1)C1C=CC=CC=1>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:8][CH2:9][C@@H:10]1[C@@H:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C@H:14]([C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)[C@@H:13]([O:28][C@@H:29]([C:31]2[CH:32]=[C:33]([C:41]([F:42])([F:43])[F:44])[CH:34]=[C:35]([C:37]([F:40])([F:38])[F:39])[CH:36]=2)[CH3:30])[CH2:12][CH2:11]1

Participants

4

Reactant 1

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

Product 1

HCID 86628115Ethyl (1R,2R,3S,6S)-6-(aminomethyl)-3-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-2-(4-fluorophenyl)cyclohexanecarboxylateYield 70%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of the crude oil from Step D (0.15 g, 0.24 mmol) in 40 mL ethanol was added 0.1 g (20% by weight) of 10% Pd(OH)2—C. The mixture was hydrogenated at 50 PSi for 16 hr at room temperature. The catalyst was filtered through a filter aid pad. The solvent of the filtrate was removed under vacuum to give the title compound (0.09 g) which was used without further purification. 1H-NMR (CDCl3) δ: 7.71 (1H, s), 7.20 (2H, s), 7.00 (2H, m), 6.85 (2H, m), 4.45 (1H, q, J=6.4 Hz), 3.83 (2H, m), 3.35 (1H, m), 3.00-2.86 (2H, m), 2.75 (1H, m), 2.52 (1H, t, J=11.0 Hz), 2.40 (1H, m), 2.25 (1H, m), 1.58 (1H, m), 1.40 (1H, m), 1.33 (3H, d, J=6.4 Hz), 0.88 (3H, t, J=7.1 Hz). MS: (MH)+ 536.5.

Workup

  1. filtrationThe catalyst was filtered through a filter aid pad
  2. customThe solvent of the filtrate was removed under vacuum

Sources & evidence

ORD record
ord-360542f5f4bf45d7b48799e925df1fbf
Source dataset
uspto-grants-2010_03
Patent number
US07683068B2

Reaction notes

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