Tert-butyl 4-cyanooxane-4-carboxylate → Tert-butyl 4-(aminomethyl)oxane-4-carboxylate

HRID 16576Notes

Reaction equation

HRID 16576 reaction equation
[C:1]([C:3]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2]>CO.[Ni]>[NH2:2][CH2:1][C:3]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1

Participants

4

Reactant 1

HCID 23131610Tert-butyl 4-cyanooxane-4-carboxylate

Product 1

HCID 67232834Tert-butyl 4-(aminomethyl)oxane-4-carboxylateYield 83%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 4-cyanotetrahydro-2H-pyran-4-carboxylate (18.95 g, 0.0897 mol, step 1) and Raney Ni (1.00 g) in methanol (200 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 16.01 g (83%) 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-cf6451dbc6644fd1a0ae0403fdb3b195
Source dataset
uspto-grants-2010_06
Patent number
US07737163B2

Reaction notes

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