Reaction #62391

Reaction equation

N-methyl-hydrazine carboxylic acid tert-butyl ester

sodium hydroxide

benzyl chloroformate

→

title compound

N′-benzyloxycarbonyl-N-methyl-hydrazine carboxylic acid tert-butyl ester

Solvents

chloroform

Conditions

Workup

1. 1
   ExtractionAdding water, extracting with chloroform
2. 2
   Washthe resultant organic layer was washed with saturated brine
3. 3
   Dryingdried over magnesium sulfate
4. 4
   OtherThe solvent was evaporated
5. 5
   Otherfollowed by purification by silica gel column chromatography (ethyl acetate:hexane=1:4)

Procedure

13.5 g of N-methyl-hydrazine carboxylic acid tert-butyl ester was dissolved in 90 mL of chloroform, added with 90 mL of 1N sodium hydroxide aqueous solution and 28 mL of benzyl chloroformate, and stirred at room temperature for 6 days. Adding water, extracting with chloroform, and the resultant organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, followed by purification by silica gel column chromatography (ethyl acetate:hexane=1:4), to afford 17.7 g of the title compound as a colorless oil.

Source