HCID 66998378, compound → (3R,4R)-4-Amino-3-methyl-piperidine-1-carboxylic acid tert-butyl ester

HRID 561268Notes

Reaction equation

HRID 561268 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 66998378HCID 66998378, compound

Product 1

HCID 66998328(3R,4R)-4-Amino-3-methyl-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

(3R,4R)-3-Methyl-4-(1-(s)-phenyl-ethylamino)-piperidine-1-carboxylic acid tert-butyl ester (810 mg, 2.55 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 give the title compound as a clear oil. Wt.: 500 mg (92%). 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-07e9a9c1e87844d0b9a2c83256fd9134
Source dataset
uspto-grants-2011_11
Patent number
US08063222B2

Reaction notes

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