rac-tert-Butyl ((1-benzyl-3-methyl-1,2,5,6-tetrahydropyridin-2-yl)methyl)carbamate → trans-N-Boc-1-(3-methylpiperidin-2-YL)methanamine

HRID 60853Notes

Reaction equation

HRID 60853 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]=[C:10]([CH3:14])[CH:9]1[CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])C1C=CC=CC=1>[OH-].[OH-].[Pd+2]>[CH3:14][C@@H:10]1[CH2:11][CH2:12][CH2:13][NH:8][C@H:9]1[CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20]

Participants

3

Reactant 1

HCID 117732713rac-tert-Butyl ((1-benzyl-3-methyl-1,2,5,6-tetrahydropyridin-2-yl)methyl)carbamate

Product 1

HCID 95378399trans-N-Boc-1-(3-methylpiperidin-2-YL)methanamine

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

A mixture of rac-tert-butyl ((1-benzyl-3-methyl-1,2,5,6-tetrahydropyridin-2-yl)methyl)carbamate and Pd(OH)2/C (20% wt, 0.1 eq) was pressurized to 4 bar with H2 and maintained at rt for 5 h. The mixture was filtered through diatomaceous earth and the filtrate was concentrated in vacuo to yield the title compound as a colorless oil. MS (ESI) 229.2 (M+H).

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-deffef23315c4fcbbc34e80d3baca2d1
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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