1-[(R)-Methoxycarbonylamino-cyclohexyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid benzyl ester → 1-[(R)-methoxycarbonylamino-cyciohexyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid

HRID 1008587Notes

Reaction equation

HRID 1008587 reaction equation
C([O:8][C:9]([C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:29])[C@H:17]([NH:24][C:25]([O:27][CH3:28])=[O:26])[CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:10])C1C=CC=CC=1>CO.[Pd]>[CH3:28][O:27][C:25]([NH:24][C@H:17]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[C:16]([N:12]1[CH2:13][CH2:14][CH2:15][C@H:11]1[C:9]([OH:10])=[O:8])=[O:29])=[O:26]

Participants

4

Reactant 1

HCID 538551711-[(R)-Methoxycarbonylamino-cyclohexyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid benzyl ester

Product 1

HCID 229584911-[(R)-methoxycarbonylamino-cyciohexyl-acetyl]-pyrrolidine-2-(S)-carboxylic acidYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.17 g 1-[(R)-methoxycarbonylamino-cyclohexyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid benzyl ester were dissolved in 90 mL of methanol and hydrogenated for 3 h at room temperature using 0.8 g palladium on charcoal (10%) as catalyst. Filtration followed by concentration in vacuo affords 0.80 g (89%) of the title compound as a colorless oil.

Workup

  1. filtrationFiltration
  2. concentrationfollowed by concentration in vacuo

Sources & evidence

ORD record
ord-fc88ed0d08df4a2c8ac9b8cd8fa2ae3a
Source dataset
uspto-grants-2004_09
Patent number
US06797710B2

Reaction notes

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