tert-butyl 4-{[(2R)-2-(benzyloxy)propanoyl]amino}piperidine-1-carboxylate → tert-butyl 4-{[(2R)-2-hydroxypropanoyl]amino}piperidine-1-carboxylate

HRID 1026542Notes

Reaction equation

HRID 1026542 reaction equation
C([O:8][C@H:9]([CH3:26])[C:10]([NH:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1)=[O:11])C1C=CC=CC=1>[C].[Pd].CO>[OH:8][C@H:9]([CH3:26])[C:10]([NH:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1)=[O:11]

Participants

4

Reactant 1

HCID 52331793tert-butyl 4-{[(2R)-2-(benzyloxy)propanoyl]amino}piperidine-1-carboxylate

Product 1

HCID 68500407tert-butyl 4-{[(2R)-2-hydroxypropanoyl]amino}piperidine-1-carboxylateYield 100.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

At room temperature, to a methanol solution (200 ml) of tert-butyl 4-{[(2R)-2-(benzyloxy)propanoyl]amino}piperidine-1-carboxylate (6.90 g) was added 10% palladium carbon (2.03 g), followed by stirring overnight under a hydrogen atmosphere. The reaction solution was filtered through Celite, and then concentrated under reduced pressure to afford tert-butyl 4-{[(2R)-2-hydroxypropanoyl]amino}piperidine-1-carboxylate (5.19 g).

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6504e2b6ee51466a8d70bdf03f882fda
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

Loading…