Acetonitrile → HCID 102434356, compound

HRID 1749536Notes

Reaction equation

HRID 1749536 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:6][C@@H:5]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:4]1([CH3:19])[CH3:18].I([O-])(=O)(=O)=[O:21].[Na+].C(#N)C>C(Cl)(Cl)(Cl)Cl.O.O.[Ru](Cl)(Cl)Cl>[CH2:10]([O:9][C:8]([NH:7][C@@H:5]1[CH2:6][C@H:3]([C:2]([OH:21])=[O:1])[C:4]1([CH3:19])[CH3:18])=[O:17])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 3

HCID 6342AcetonitrileHCID 23667635Sodium periodateHCID 131733593HCID 131733593, compound

Product 1

HCID 102434356HCID 102434356, compoundYield 90.1%

Reagents, catalysts & solvents 3

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 962WaterSolvent2×HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of benzyl ((1R,3S)-3-(hydroxymethyl)-2,2-dimethylcyclobutyl)carbamate (2.75 g, 10.4 mmol) in carbon tetrachloride (14 mL) was added sodium periodate (6.68 g, 31.2 mmol), water (21 mL) and acetonitrile (14 mL), followed by ruthenium(III) chloride hydrate (52 mg, 0.2 mmol, in 0.5 mL of water) at room temperature. The resulting biphasic mixture was stirred vigorously at room temperature for 1 h. The reaction mixture was diluted with water and extracted with DCM (2×150 mL). The combined organic layers were dried over sodium sulfate and concentrated to give the title compound (2.6 g, crude), which was used directly in the next step without further purification. MS (ESI) m/z 278.1 [M+H]+.

Workup

  1. extractionextracted with DCM (2×150 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a6faf2c91fe74dc2aaf53e477d701b33
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

Loading…