tert-butyl 4-[(4-cyanopiperidin-1-yl)methyl]tetrahydro-2H-pyran-4-carboxylate → tert-Butyl4-{[4-(aminomethyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylate

HRID 736404Notes

Reaction equation

HRID 736404 reaction equation
[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH2:5][CH2:4]1)#[N:2]>CO.[Ni]>[NH2:2][CH2:1][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH2:5][CH2:4]1

Participants

4

Reactant 1

HCID 67232740tert-butyl 4-[(4-cyanopiperidin-1-yl)methyl]tetrahydro-2H-pyran-4-carboxylate

Product 1

HCID 67232551tert-Butyl4-{[4-(aminomethyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylateYield 98%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 4-[(4-cyanopiperidin-1-yl)methyl]tetrahydro-2H-pyran-4-carboxylate (5.76 g, 0.0187 mol, step 4) and Raney Ni (3.00 g) in methanol (100 mL) was hydrogenated (3 atm) at room temperature for 12 h. Then, the mixture was filtered through a pad of Celite, and the filtrate was concentrated in vacuo to give 5.72 g (98%) of the title compound as a yellow syrup.

Workup

  1. customat room temperature
  2. customfor 12 h
  3. filtrationThen, the mixture was filtered through a pad of Celite
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-367204b420c04dcfb15b17565f218943
Source dataset
uspto-grants-2009_09
Patent number
US07595329B2

Reaction notes

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