1-(Propylsulfonyl)-3-pyridin-2-ylazetidine-3-carbonitrile → 1-[1-(Propylsulfonyl)-3-pyridin-2-ylazetidin-3-yl]methanamine

HRID 2100308Notes

Reaction equation

HRID 2100308 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

HCID 577983111-(Propylsulfonyl)-3-pyridin-2-ylazetidine-3-carbonitrile

Product 1

HCID 577983191-[1-(Propylsulfonyl)-3-pyridin-2-ylazetidin-3-yl]methanamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

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.

Workup

  1. filtrationthe reaction was filtered through Celite (MeOH wash)
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-327c8255fdd34c21be39caec9098d427
Source dataset
uspto-grants-2009_08
Patent number
US07572792B2

Reaction notes

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