1-(SR)-(3,5-Bis(trifluoromethyl)phenyl)methoxy-2-(SR)-phenyl-3-(RS)-(benzyloxycarbonylamino)cyclopentane → HCID 75024257, compound

HRID 1017759Notes

Reaction equation

HRID 1017759 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][CH:15]2[CH2:19][CH2:18][CH:17]([NH:20]C(OCC3C=CC=CC=3)=O)[CH:16]2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1>CO.[Pd]>[F:1][C:2]([F:37])([F:38])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][CH:15]2[CH2:19][CH2:18][CH:17]([NH2:20])[CH:16]2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

4

Reactant 1

HCID 750242431-(SR)-(3,5-Bis(trifluoromethyl)phenyl)methoxy-2-(SR)-phenyl-3-(RS)-(benzyloxycarbonylamino)cyclopentane

Product 1

HCID 75024257HCID 75024257, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 200 mg of 1-(SR)-(3,5-bis(trifluoromethyl)phenyl)methoxy-2-(SR)-phenyl-3-(RS)-(benzyloxycarbonylamino)cyclopentane prepared in Example 4, Step B in 5 mL of methanol was hydrogenated over 50 mg of 10% Pd/C for 2 hours. The reaction was filtered and concentrated. The residue was purified on a 1 mm preparative silica gel plate eluted with 10% MeOH in ethyl acetate to obtain 120 mg of title compound. Mass spec (NH3/CI): 404 (M+1).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. customThe residue was purified on a 1 mm preparative silica gel plate
  4. washeluted with 10% MeOH in ethyl acetate

Sources & evidence

ORD record
ord-333d7b65bb0e49fe94c2e688fd55e2fe
Source dataset
uspto-grants-2002_11
Patent number
US06479518B2

Reaction notes

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