Water → (R)-1-Boc-3-cyanopyrrolidine

HRID 2228767Notes

Reaction equation

HRID 2228767 reaction equation
[C-:1]#[N:2].[K+].CS(O[C@H:9]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]1)(=O)=O.O>CS(C)=O>[C:1]([C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]1)#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 11032777(S)-1-Boc-3-methanesulfonyloxy-pyrrolidine

Product 1

HCID 7018344(R)-1-Boc-3-cyanopyrrolidineYield 62%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium cyanide (5.80 g, 89.0 mmol) was added to a solution of tert-butyl (3S)-3-[(methylsulphonyl)oxy]-1-pyrrolidinecarboxylate (preparation 78) (9.35 g, 35.3 mmol) in dimethylsulphoxide (100 ml), and the reaction stired at room temperature for 18 hrs, and then at 100° C. for a further 24 hrs. The cooled mixture was poured into water and extracted well with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate:pentane (20:80) as eluant to give the title compound as an oil, (4.28 g, 62%).

Workup

  1. waitat 100° C. for a further 24 hrs
  2. extractionextracted well with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-a46104ec93c44146a2acb9f1e833c7b2
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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