Water → (S)-1-Boc-3-cyanopyrrolidine

HRID 1029634Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10](OS(C)(=O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C-:18]#[N:19].[Na+].C(OCC)(=O)C.O>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([C:18]#[N:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (R)-1-t-butoxycarbonyl-3-methanesulfonyloxypyrrolidine (20 g) in dimethyl sulfoxide (200 ml) was added sodium cyanide (11 g) at ambient temperature under nitrogen. After stirring at 100° C. under nitrogen for 1 hour, the solution was taken up into a mixture of ethyl acetate and water. The organic layer was separated, and washed with water and brine successively. The dried solvent was evaporated, and the residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (2:1, V/V) to give (S)-1-t-butoxycarbonyl-3-cyanopyrrolidine (9.0 g).

Workup

customThe organic layer was separated
washwashed with water and brine successively
customThe dried solvent was evaporated
customthe residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (2:1, V/V)

Sources & evidence

ORD record: ord-f50117b4758248b9b059e11e0026cde1
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05102877

Reaction notes

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