Tert-butyl trans-1-benzyl-4-methylpiperidin-3-ylcarbamate → trans-tert-Butyl (4-methylpiperidin-3-yl)carbamate

HRID 1923676Notes

Reaction equation

HRID 1923676 reaction equation
C([N:8]1[CH2:13][CH2:12][C@@H:11]([CH3:14])[C@H:10]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:9]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH3:14][C@@H:11]1[CH2:12][CH2:13][NH:8][CH2:9][C@H:10]1[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 2

HCID 67045797Tert-butyl trans-1-benzyl-4-methylpiperidin-3-ylcarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 57931128trans-tert-Butyl (4-methylpiperidin-3-yl)carbamateYield 95.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl trans-1-benzyl-4-methylpiperidin-3-ylcarbamate (0.64 g, 2.1 mmol) and 10% Pd/C (0.22 g, 0.21 mmol) in methanol (10 mL) was charged with 1 atmosphere hydrogen and stirred at room temperature for 18 hours. The catalyst was removed by filtration and washed with methanol (20 mL). The filtrate was concentrated in vacuo to give tert-butyl trans-4-methylpiperidin-3-ylcarbamate (0.43 g, 95%) as a solid.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with methanol (20 mL)
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-38c2348c799f48e4a3e749287dea01dc
Source dataset
uspto-grants-2012_05
Patent number
US08178131B2

Reaction notes

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