N-Boc-N-[(1-Cbz-4-piperidyl)methyl]cyclopropanamine → tert-butyl N-cyclopropyl-N-[(piperidin-4-yl)methyl]carbamate

HRID 220839Notes

Reaction equation

HRID 220839 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:19]2[CH2:21][CH2:20]2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>CO.[Pd]>[C:25]([O:24][C:22](=[O:23])[N:18]([CH:19]1[CH2:20][CH2:21]1)[CH2:17][CH:14]1[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]1)([CH3:28])([CH3:26])[CH3:27]

Participants

4

Reactant 1

HCID 57555353N-Boc-N-[(1-Cbz-4-piperidyl)methyl]cyclopropanamine

Product 1

HCID 57555340tert-butyl N-cyclopropyl-N-[(piperidin-4-yl)methyl]carbamateYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-[(tert-Butoxycarbonyl-cyclopropyl-amino)-methyl]-piperidine-1-carboxylic acid benzyl ester from Example E38.2 (3.67 g, 9.4 mmol) was dissolved in methanol (100 ml) and hydrogenated over 10% Pd/C catalyst (3 g) for 1 h. The mixture was filtered through Celite® filter agent and the filtrate was concentrated in vacuo to yield the title compound (2.07 g, 87%).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. filtrationfilter agent
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6d2d5409873f46ee87973304867f7b48
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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