Sodium Cyanide → tert-butyl (2S)-2-(cyanomethyl)pyrrolidine-1-carboxylate

HRID 928014Notes

Reaction equation

[C-:1]#[N:2].[Na+].CC1C=CC(S(O[CH2:15][C@@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])(=O)=O)=CC=1>CS(C)=O.S([O-])([O-])(=O)=O.[Fe+2]>[C:1]([CH2:15][C@@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])#[N:2]

Participants

Conditions

Temperature: 90 °C

Procedure

Sodium cyanide (8.2 g) was added to a solution of tert-butyl (S)-2-(4-methylbenzenesulfonyloxymethyl)pyrrolidine-1-carboxylate (Intermediate 140, 29.6 g) in DMSO (300 mL) and the resultant mixture was stirred and heated at 90° C. for 5.5 hours. After cooling, the mixture was treated with saturated aqueous iron (II) sulphate solution and the mixture was stirred for a further 5 hours then extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and petroleum ether (5%) to give tert-butyl (S)-2-cyanomethylpyrrolidine-1-carboxylate (13.0 g) as a light yellow oil which was used without further characterisation.

Workup

temperatureAfter cooling
extractionthen extracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried (Na2SO4)
filtrationfiltered
customThe filtrate was evaporated to dryness
customthe residue was purified by chromatography on silica
washeluting with a mixture of ethyl acetate and petroleum ether (5%)

Sources & evidence

ORD record: ord-4a41f415b0d5469ba85e3ffdc94e2476
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290472B2

Reaction notes

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