Water → HCID 57619809, compound

HRID 1642493Notes

Reaction equation

HRID 1642493 reaction equation
CS(O[CH2:6][C@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@@H:8]1[NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])(=O)=O.[C-:21]#[N:22].[K+].O>CS(C)=O>[C:21]([CH2:6][C@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@@H:8]1[NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])#[N:22]

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 59025455HCID 59025455, compound

Product 1

HCID 57619809HCID 57619809, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of tert-butyl N-[(1S,2S)-2-(methylsulfonyloxymethyl)cyclohexyl]carbamate (1.8 g) in dry DMSO was added with potassium cyanide (0.52 g, 7.76 mL) and the mixture was then heated at 90° C. under N2 for 4 hours. The mixture was cooled and then poured on to water (50 mL) and extracted with ether (3×30 mL). The combined organic phases were washed with brine and concentrated in vacuo to provide the title compound.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ether (3×30 mL)
  3. washThe combined organic phases were washed with brine
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3468f71506284219a5ae7cf81dfa10ec
Source dataset
uspto-grants-2012_02
Patent number
US08119661B2

Reaction notes

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