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

HRID 733080Notes

Reaction equation

HRID 733080 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 of Example 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 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-21888b34486c40e79af02ddc501393c6
Source dataset
uspto-grants-2009_09
Patent number
US07589109B2

Reaction notes

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