HCID 53917917, compound → HCID 54546026, compound

HRID 1276357Notes

Reaction equation

HRID 1276357 reaction equation
[C:1]([O:5][C:6]([NH:8][N:9]1[CH2:13][CH2:12][C@H:11]([C:14]#[N:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[NH4+].[OH-].CO.[Ni]>[C:1]([O:5][C:6]([NH:8][N:9]1[CH2:13][CH2:12][C@@H:11]([CH2:14][NH2:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 53917917HCID 53917917, compound

Product 1

HCID 54546026HCID 54546026, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21894508Ammonium hydroxide methanolSolvent

Procedure

A solution of (S)-1-(tert-butoxycarbonylamino)-3-cyanopyrrolidine (13.5g, 67 mmol) in 50 mL of 3% NH4OH/methanol and Raney Nickel (0.5 g, 50% slurry in water) was pressurized to 40 psi under H2 atmosphere. After stirring for 12 h at room temperature, the reaction mixture was filtered through a pad of Celite and the residue was washed with 100 mL of methanol. The filtrate was concentrated to dryness to give an oil (S)-1-(tert-butoxycarbonylamino)-3-aminomethylpyrrolidine (10 g).

Workup

  1. filtrationthe reaction mixture was filtered through a pad of Celite
  2. washthe residue was washed with 100 mL of methanol
  3. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-97a0b19b1f75432f89100e19d90a96b1
Source dataset
uspto-grants-2000_12
Patent number
US06166015

Reaction notes

Loading…