1-[2-(2-Benzyloxycarbonylamino-2-cyclohexyl-acetylamino)-3,3-dimethyl-butyryl]-octahydroindole-2-carboxylic acid tert-butyl ester → 1-[2-(2-Amino-2-cyclohexyl-acetylamino)-3,3-dimethyl-butyryl]-octahydro-indole-2-carboxylic acid tert-butyl ester

HRID 917799Notes

Reaction equation

HRID 917799 reaction equation
[C:1]([O:5][C:6]([CH:8]1[CH2:16][CH:15]2[CH:10]([CH2:11][CH2:12][CH2:13][CH2:14]2)[N:9]1[C:17](=[O:44])[CH:18]([NH:23][C:24](=[O:43])[CH:25]([NH:32]C(OCC1C=CC=CC=1)=O)[CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C:19]([CH3:22])([CH3:21])[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([CH:8]1[CH2:16][CH:15]2[CH:10]([CH2:11][CH2:12][CH2:13][CH2:14]2)[N:9]1[C:17](=[O:44])[CH:18]([NH:23][C:24](=[O:43])[CH:25]([NH2:32])[CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1)[C:19]([CH3:22])([CH3:21])[CH3:20])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 684942111-[2-(2-Benzyloxycarbonylamino-2-cyclohexyl-acetylamino)-3,3-dimethyl-butyryl]-octahydroindole-2-carboxylic acid tert-butyl ester

Product 1

HCID 684969241-[2-(2-Amino-2-cyclohexyl-acetylamino)-3,3-dimethyl-butyryl]-octahydro-indole-2-carboxylic acid tert-butyl esterYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

CBz ester 15b (3.0 g, 4.9 mmol) was stirred in EtOH (25 mL) and charged with 300 mg 10%Pd(OH)2/C. H2 gas was bubbled into the suspension until the reaction was complete. Catalyst was removed by filtration and the filtrate concentrated in vacuo to give 1-[2-(2-amino-2-cyclohexyl-acetylamino)-3,3-dimethyl-butyryl]-octahydro-indole-2-carboxylic acid tert-butyl ester 16b (2.34 g, 4.9 mmol, 100%) which was used as is in the next step without further purification.

Workup

  1. customH2 gas was bubbled into the suspension until the reaction
  2. customCatalyst was removed by filtration
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-4f360f164b12416aa67c2e648c20122c
Source dataset
uspto-grants-2007_09
Patent number
US07273885B2

Reaction notes

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