3-Benzyloxycarbonylamino-3-(2-hydroxy-1-methylethyl)piperidine-1-carboxylic acid tert-butyl ester → 3-Amino-3-(2-hydroxy-1-methylethyl)piperidine-1-carboxylic acid tert-butyl ester

HRID 1912382Notes

Reaction equation

HRID 1912382 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([NH:18]C(OCC2C=CC=CC=2)=O)([CH:14]([CH3:17])[CH2:15][OH:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[C].[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([NH2:18])([CH:14]([CH3:17])[CH2:15][OH:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 582933703-Benzyloxycarbonylamino-3-(2-hydroxy-1-methylethyl)piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 582932813-Amino-3-(2-hydroxy-1-methylethyl)piperidine-1-carboxylic acid tert-butyl esterYield 99.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of an optically-active compound of 3-benzyloxycarbonylamino-3-(2-hydroxy-1-methylethyl)piperidine-1-carboxylic acid tert-butyl ester (21.0 g) in methanol (400 ml) was added 10% palladium carbon (2.1 g), and the mixture was hydrogenated at room temperature under ordinary pressure for 90 minutes. The mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure to give the titled compound (13.8 g).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f73884892a9a432baefd93c4084421a6
Source dataset
uspto-grants-2013_12
Patent number
US08609647B2

Reaction notes

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