HCID 66997280, compound → (3S,4S)-4-Amino-3-methyl-piperidine-1-carboxylic acid tert-butyl ester

HRID 1726456Notes

Reaction equation

HRID 1726456 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C@@H](C2C=CC=CC=2)C)[C@@H:10]([CH3:23])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[Pd+2].[OH-]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([NH2:14])[C@@H:10]([CH3:23])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 66997280HCID 66997280, compound

Product 1

HCID 66998410(3S,4S)-4-Amino-3-methyl-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

(3S, 4S)-3-Methyl-4-(1-(R)-phenyl-ethylamino)-piperidine-1-carboxylic acid tert-butyl ester (510 mg, 1.60 mmol) was dissolved in methanol (15 mL). Palladium hydroxide (20%, 100 mg) was added and the mixture was shaken under a hydrogen atmosphere overnight at 55 psi. The reaction was filtered and concentrated in vacuo to provide the title compound as a clear oil. Wt.: 320 mg (88%). NMR (300 MHz, CDCl3) δ 4.06 (m, 1H), 3.96 (m, 1H), 2.73 (m, 1H), 2.34 (m, 2H), 1.77 (m, 1H), 1.43 (s, 9H), 1.27 (m, 2H), 0.94 (d, 3H); LC/MS m/z 215 (M+H)+.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fc1ba1c62dbc4587b112f942559876a0
Source dataset
uspto-grants-2009_02
Patent number
US07491827B2

Reaction notes

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