Sodium Cyanide → HCID 52420731, compound

HRID 928064Notes

Reaction equation

HRID 928064 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]2[CH2:17][CH2:16][N:15]([C:18]([O-:20])=[O:19])[CH2:14]2)(=O)=O)=CC=1.[C-:21]#[N:22].[Na+]>CS(C)=O.S([O-])([O-])(=O)=O.[Fe+2]>[C:21]([CH2:12][C@@H:13]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:13]([CH3:17])([CH3:14])[CH3:12])=[O:19])[CH2:14]1)#[N:22]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 86713363HCID 86713363, compound2×

Product 1

HCID 52420731HCID 52420731, compoundYield 156.5%

Reagents, catalysts & solvents 2

HCID 24393Ferrous SulfateCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of tert-butyl ((R)-3-(4-methylbenzenesulfonyloxymethyl)pyrrolidine-1-carboxylate (Intermediate 207, 22.3 g) and sodium cyanide (6.13 g) in DMSO (100 mL) was stirred and heated at 100° C. for 4 hours. After cooling, a saturated aqueous solution of iron (II) sulphate was added and the mixture was stirred at room temperature for 8 hours. The resultant mixture was extracted with ethyl acetate, washed with brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with an mixture of ethyl acetate and petroleum ether (20%) to give tert-butyl (S)-3-cyanomethylpyrrolidine-1-carboxylate (12.3 g) as a white solid which was used without further characterisation.

Workup

  1. temperatureAfter cooling
  2. stirringthe mixture was stirred at room temperature for 8 hours
  3. extractionThe resultant mixture was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was purified by chromatography on silica
  9. washeluting with an mixture of ethyl acetate and petroleum ether (20%)

Sources & evidence

ORD record
ord-f745d7c0162447a6a103b6b64e9a4b66
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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