Potassium Hydroxide → HCID 91243547, compound

HRID 2261906Notes

Reaction equation

HRID 2261906 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C@@:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:11])[CH:9]=[O:10])([CH3:4])([CH3:3])[CH3:2].[I-].[CH3:21][S+](C)C.[OH-].[K+]>C(#N)C.O.CCOC(C)=O>[C:1]([O:5][C:6](=[O:19])[NH:7][C@@:8]([CH3:11])([CH:9]1[CH2:21][O:10]1)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 75127Trimethylsulfonium iodide2×HCID 58990158HCID 58990158, compound

Product 1

HCID 91243547HCID 91243547, compound

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-(tert-butyl((1R)-1-benzyl-1-methyl-2-oxoethyl)carbamate (Intermediate XLIX, 1 g, 3.80 mmol) in acetonitrile (15 mL) was added 6 drops water, trimethylsulfonium iodide (775 mg, 3.80 mmol) and potassium hydroxide (511 mg, 9.11 mmol). The reaction was stirred at 60° C., sealed, for 1.5 h, additional trimethylsulfonium iodide (775 mg, 3.80 mmol) and potassium hydroxide (511 mg, 9.11 mmol) were added and the reaction was stirred at 60° C., sealed, for 3 h. the reaction mixture was diluted with EtOAc, washed with sat'd aq NaHCO3, brine, dried over sodium sulfate, and concentrated in vacuo to provide tert-butyl((1R)-1-methyl-1-oxiran-2-yl-2-phenylethyl)carbamate as an oil. MS (ES, M+H) 278.

Workup

  1. customsealed, for 1.5 h
  2. stirringthe reaction was stirred at 60° C.
  3. customsealed, for 3 h. the reaction mixture
  4. washwashed with sat'd aq NaHCO3, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f035d7908793461da60b64ffcdc1ff56
Source dataset
uspto-grants-2010_12
Patent number
US07847100B2

Reaction notes

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