Benzyl chloroformate → 2-Benzyl 1-tert-butyl 1-methylhydrazine-1,2-dicarboxylate

HRID 34113

Reaction equation

HRID 34113 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:10])[NH2:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]([CH3:10])[NH:9][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 37482801-Boc-1-methylhydrazine

Product 1

HCID 451584202-Benzyl 1-tert-butyl 1-methylhydrazine-1,2-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

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.

Workup

  1. extractionAdding water, extracting with chloroform
  2. washthe resultant organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated
  5. customfollowed by purification by silica gel column chromatography (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-386231fe66e54a26bac7d782698e1a68
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Linked notes

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