Tert-butyl trans-1-benzyl-4-cyclopropylpiperidin-3-ylcarbamate → Tert-butyl-trans-4-cyclopropylpiperidin-3-ylcarbamate

HRID 408155Notes

Reaction equation

HRID 408155 reaction equation
C([N:8]1[CH2:13][CH2:12][C@@H:11]([CH:14]2[CH2:16][CH2:15]2)[C@H:10]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:9]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[C:20]([O:19][C:18](=[O:24])[NH:17][C@H:10]1[C@H:11]([CH:14]2[CH2:15][CH2:16]2)[CH2:12][CH2:13][NH:8][CH2:9]1)([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 2

HCID 67045345Tert-butyl trans-1-benzyl-4-cyclopropylpiperidin-3-ylcarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 86652140Tert-butyl-trans-4-cyclopropylpiperidin-3-ylcarbamateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl trans-1-benzyl-4-cyclopropylpiperidin-3-ylcarbamate (1.20 g, 3.63 mmol) and 10% Pd/C (0.39 g, 0.36 mmol) in methanol (20 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-cyclopropylpiperidin-3-ylcarbamate (0.87 g, 100%) 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-d4791c2fe61048bf86551e37be760f5c
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Reaction notes

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