Benzyl 3-((tert-butoxycarbonyl)amino)-3-methylpiperidine-1-carboxylate → Tert-butyl (3-methylpiperidin-3-yl)carbamate

HRID 1923756Notes

Reaction equation

HRID 1923756 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([CH3:25])[CH2:14][CH2:13][CH2:12][N:11](C(OCC2C=CC=CC=2)=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[CH3:25][C:9]1([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]1

Participants

4

Reactant 1

HCID 60205232Benzyl 3-((tert-butoxycarbonyl)amino)-3-methylpiperidine-1-carboxylate

Product 1

HCID 19691473Tert-butyl (3-methylpiperidin-3-yl)carbamateYield 72.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl 3-(tert-butoxycarbonylamino)-3-methylpiperidine-1-carboxylate (1.4 g, 4.0 mmol) and 10% Pd/C (0.21 g, 0.2 mmol) in MeOH (20 mL) were stirred under an H2 atmosphere (1 atm) for 1 hour. The catalyst was removed by filtration and washed with methanol. The filtrate was concentrated to give tert-butyl 3-methylpiperidin-3-ylcarbamate (0.62 g, 72% yield) as a solid.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-bc7d14904bbb44f0beeb8046db4a71d1
Source dataset
uspto-grants-2012_05
Patent number
US08178131B2

Reaction notes

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