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

HRID 408148Notes

Reaction equation

HRID 408148 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-067e194c018d4d29a406d82d2d1fea2e
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Reaction notes

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