1-(Propylsulfonyl)-3-pyridin-2-ylazetidine-3-carbonitrile → 1-[1-(Propylsulfonyl)-3-pyridin-2-ylazetidin-3-yl]methanamine
Reaction equation
[CH2:1]([S:4]([N:7]1[CH2:10][C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)([C:11]#[N:12])[CH2:8]1)(=[O:6])=[O:5])[CH2:2][CH3:3]>N.CO.[Ni]>[CH2:1]([S:4]([N:7]1[CH2:10][C:9]([CH2:11][NH2:12])([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:8]1)(=[O:5])=[O:6])[CH2:2][CH3:3]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 1-(propylsulfonyl)-3-pyridin-2-ylazetidine-3-carbonitrile (II-1, 379 mg, 1.43 mmol) in 2 M NH3/MeOH (50 mL) was treated with excess Raney Ni and agitated under an atmosphere of H2 (40 psi) in a Parr apparatus. After 5 h, the reaction was filtered through Celite (MeOH wash) and concentrated under reduced pressure to afford 1-[1-(propylsulfonyl)-3-pyridin-2-ylazetidin-3-yl]methanamine (II-2) as a yellow oil. Analytical LCMS: single peak (214 nm), 1.791 min. This material was used in subsequent reactions without further purification.