Methylhydrazine → 1-Boc-1-methylhydrazine

HRID 1437860Notes

Reaction equation

HRID 1437860 reaction equation
[C:1]([O:5][C:6]([O:8]C(OC(C)(C)C)=O)=O)([CH3:4])([CH3:3])[CH3:2].[CH3:16][NH:17][NH2:18].CO.ClCCl>CO>[C:1]([O:5][C:6]([N:17]([CH3:16])[NH2:18])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 90495Di-tert-butyl dicarbonateHCID 21226129Dichloromethane methanol

Product 1

HCID 37482801-Boc-1-methylhydrazineYield 92.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
5 °C

Procedure

Di-tert-butyl-dicarbonate (0.23.69 g, 108.5 mmol) in methanol (40 mL) was added dropwise over a period of 1.5 h to a solution of methylhydrazine (5.00 g, 106.4 mmol) in methanol (20 mL) cooled to ˜5° C. When the addition was complete, tlc (10% methanol/dichloromethane) indicated that the reaction was complete. The reaction mixture was stored at −20° C. overnight, and then the solvent was evaporated to give N-methyl-hydrazinecarboxylic acid tert-butyl ester (14.34 g, 92%) as a colorless oil which was used directly in the subsequent step without further purification.

Workup

  1. additionWhen the addition
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-3dbcc68fa70945deb12f7059960ed119
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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