tert-Butyl (3R)-3-{[(benzyloxy)carbonyl]amino}piperidine-1-carboxylate → tert-butyl (3R)-3-aminopiperidine-1-carboxylate

HRID 496662Notes

Reaction equation

HRID 496662 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:14]C(OCC2C=CC=CC=2)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([NH2:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 51656152tert-Butyl (3R)-3-{[(benzyloxy)carbonyl]amino}piperidine-1-carboxylate

Product 1

HCID 1501974tert-butyl (3R)-3-aminopiperidine-1-carboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a slurry of Pd—C (10%, 170 mg) in MeOH (2 ml) was added a solution of the 3(R)-Benzyloxycarbonylamino-piperidine-1-carboxylic acid tert-butyl ester (1.0 g) in MeOH (60 ml). The mixture was stirred under H2 (1 atm) for 8 hr. After being filtered through Celite, the filtrate was evaporated to give a light yellow oil (572 mg, 99%). 1H-NMR (300 MHz, CDCl3) δ 4.00-3.78 (m, 2H), 3.80 (m, 2H), 3.60 (m, 1H), 1.90 (m, 1H), 1.70 (m, 1H), 1.60-1.40 (m, 12H), 1.30 (m, 1H) ppm; IR (film) 3485, 3361, 3292, 2975, 22931, 2862, 1692, 1608, 1548, 1479, 1427, 1367, 1266, −1242, 1162 cm−1; LRMS (calculated for C10H20N2O2) 200. found 200.

Workup

  1. filtrationAfter being filtered through Celite
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-09d41855664f415a896078dd872b7d21
Source dataset
uspto-grants-2005_09
Patent number
US06946477B2

Reaction notes

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