4-Benzyloxycarbonylamino-4-hydroxymethyl piperidine-1-carboxylic acid tert-butyl ester → tert-Butyl 4-amino-4-(hydroxymethyl)piperidine-1-carboxylate

HRID 39700Notes

Reaction equation

C(OC([NH:11][C:12]1([CH2:25][OH:26])[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)=O)C1C=CC=CC=1>[OH-].[Pd+2].[OH-].[C].C(O)C>[NH2:11][C:12]1([CH2:25][OH:26])[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:14][CH2:13]1

Participants

Conditions

Temperature: 40 °C

Procedure

To 10 mL of an ethanol solution containing 0.55 g of tert-butyl 4-(((benzyloxy)carbonyl)amino)-4-(hydroxymethyl)piperidine-1-carboxylate, 0.10 g of 20% palladium hydroxide-carbon was added at room temperature, and the mixture was stirred at 40° C. for 3 hours under a hydrogen atmosphere. The insoluble material filtered off, and the filtration residue thus obtained was washed 3 times with chloroform. The filtrate and the washing solution were combined, and the solvent was removed under reduced pressure to obtain 0.39 g of a dark brown oily substance, tert-butyl 4-amino-4-(hydroxymethyl)piperidine-1-carboxylate.

Workup

additionwas added at room temperature
filtrationThe insoluble material filtered off
customthe filtration residue thus obtained
washwas washed 3 times with chloroform
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-c24a0a827f9e4dfc85ef3b68c16bd8a9
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524738B2

Reaction notes

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