Sodium Iodide → HCID 131733489, compound

HRID 2279577Notes

Reaction equation

HRID 2279577 reaction equation
CS(O[CH2:6][CH2:7][C@@H:8]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH:16]([F:18])[F:17])=[CH:11][CH:10]=1)(=O)=O.[C-:27]#[N:28].[Na+].[Na+].[I-]>CS(C)=O.O>[C:27]([CH2:6][CH2:7][C@@H:8]([NH:19][C:20](=[O:21])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH:16]([F:18])[F:17])=[CH:11][CH:10]=1)#[N:28]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 8929Sodium CyanideHCID 131733488HCID 131733488, compound

Product 1

HCID 131733489HCID 131733489, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of 388 in DMSO (5 mL) was added NaCN (92.0 mg, 1.88 mmol) and NaI (25.6 mg, 0.171 mmol) and the mixture heated at 85° C. overnight. After cooling to RT, the mixture was diluted with H2O (100 mL), stirred for 30 min and filtered to afford a tan solid. The solid was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (0 to 25% EtOAc) to afford 261 mg (47%) of (R)-tert-butyl 3-cyano-1-(4-(difluoromethoxy)phenyl)propylcarbamate (390) as a white solid.

Workup

  1. temperatureAfter cooling to RT
  2. filtrationfiltered
  3. customto afford a tan solid
  4. customThe solid was purified by SiO2 chromatography
  5. washeluting with an EtOAc/hexane gradient (0 to 25% EtOAc)

Sources & evidence

ORD record
ord-4192b5a4dca34585bd932b1afc43140a
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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