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 733083Notes

Reaction equation

HRID 733083 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]>[C:19]([O:18][C:16]([C:10]1([CH2:9][N:6]2[CH2:7][CH2:8][CH:3]([CH2:1][NH2:2])[CH2:4][CH2:5]2)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)=[O:17])([CH3:22])([CH3:21])[CH3:20]

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]tetra hydro-2H-pyran-4-carboxylate (5.76 g, 0.0187 mol, step 4 of Example 1) 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 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-c70be2156f4c458c8b6c015785e51132
Source dataset
uspto-grants-2009_09
Patent number
US07589109B2

Reaction notes

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