4-Tert-butoxycarbonylamino-4-cyclohexyl-but-2-enoic acid methyl ester → 4-Tert-butoxycarbonylamino-4-cyclohexyl-butyric acid methyl ester

HRID 491870Notes

Reaction equation

HRID 491870 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH:4]=[CH:5][CH:6]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][CH:6]([NH:13][C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

4

Reactant 1

HCID 670235054-Tert-butoxycarbonylamino-4-cyclohexyl-but-2-enoic acid methyl ester

Product 1

HCID 670235234-Tert-butoxycarbonylamino-4-cyclohexyl-butyric acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-tert-butoxycarbonylamino-4-cyclohexyl-but-2-enoic acid methyl ester (9 g, 30 mmol) in MeOH (100 mL) was added Pd—C (10% on activated carbon) (1 g) under N2, and the reaction mixture was subjected to hydrogenation under 20 psi for 4 hours. The catalyst was filtered out, and the MeOH was evaporated to yield 4-tert-butoxycarbonylamino-4-cyclohexyl-butyric acid methyl ester as a white solid.

Workup

  1. filtrationThe catalyst was filtered out
  2. customthe MeOH was evaporated

Sources & evidence

ORD record
ord-e0b261f5468e4990a47b3b4aa2c64ac7
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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