Methyl iodide → HCID 18639181, compound

HRID 1650279Notes

Reaction equation

HRID 1650279 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([NH:12][C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14])[CH2:9][C@H:8]1[CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])=[O:6])[CH:2]=[CH2:3].[H-].[Na+].[CH3:30]I>CN(C)C=O.O.C(OCC)(=O)C>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([N:12]([C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14])[CH3:30])[CH2:9][C@H:8]1[CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:22])[CH3:23])=[O:6])[CH:2]=[CH2:3]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57112577HCID 57112577, compound

Product 1

HCID 18639181HCID 18639181, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,4S)-1-allyloxycarbonyl-4-(allyloxycarbonylamino)-2-t-butyldimethylsilyloxymethylpyrrolidine (0.97 g) in N,N-dimethylformamide (5.0 ml) was added sodium hydride (0.099 g) at 0° C. After stirring at ambient temperature for 1 hour, the mixture was cooled to 0° C. To the mixture was added methyl iodide (0.31 ml) and the resulting mixture was stirred for additional 4 hours at 0° C. The reaction mixture was diluted with water (50 ml) and ethyl acetate (50 ml). The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated to give (2S,4S)-1-allyloxycarbonyl-4-(N-allyloxycarbonyl-N-methylamino)-2-t-butyldimethylsilyloxymethylpyrrolidine (1.01 g). IR (Neat): 1700 cm-1

Workup

  1. temperaturethe mixture was cooled to 0° C
  2. stirringthe resulting mixture was stirred for additional 4 hours at 0° C
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-20479198139b491a940ba0cf27057212
Source dataset
uspto-grants-1990_05
Patent number
US04923857

Reaction notes

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