Ethyl Acetate → HCID 75024269, compound

HRID 1017761Notes

Reaction equation

HRID 1017761 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][CH:15]2[CH2:19][CH2:18][CH:17]([N:20](C(OCC3C=CC=CC=3)=O)[CH3:21])[CH:16]2[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(OCC)(=O)C>CO.[Pd]>[F:1][C:2]([F:38])([F:39])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][CH:15]2[CH2:19][CH2:18][CH:17]([NH:20][CH3:21])[CH:16]2[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 865848721-(SR)-(3,5-Bis(trifluoromethyl)phenyl)methoxy-2-(SR)-phenyl-3-(RS)-(N-(benzyloxycarbonyl)-N-methylamino) cyclopentane

Product 1

HCID 75024269HCID 75024269, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 475 mg of the above 1-(SR)-(3,5-bis(trifluoromethyl)-phenyl)methoxy-2-(SR)-phenyl-3-(RS)-(N-(benzyloxycarbonyl)-N-methylamino) cyclopentane in 5 mL of 1:1 methanol: ethyl acetate was hydrogenated over 100 mg of 10% Pd/C for 2 hours. The reaction was filtered and concentrated to afford the title compound as an oil. Mass spec (NH3/CI): 418 (M+1).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-160cb8ea256f4f32bf40e67074a5f408
Source dataset
uspto-grants-2002_11
Patent number
US06479518B2

Reaction notes

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