Triethylamine → N'-(2-ethoxy-phenyl)-N-methyl-hydrazinecarboxylic acid tert-butyl ester

HRID 1437987Notes

Reaction equation

HRID 1437987 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:10])[NH2:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:11]([O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1B(O)O)[CH3:12].C(N(CC)CC)C>ClCCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]([CH3:10])[NH:9][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[O:13][CH2:11][CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2734902(2-Ethoxyphenyl)boronic acidHCID 37482801-Boc-1-methylhydrazine2×

Product 1

HCID 57941442N'-(2-ethoxy-phenyl)-N-methyl-hydrazinecarboxylic acid tert-butyl esterYield 41.5%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of N-methyl-hydrazinecarboxylic acid tert-butyl ester (Intermediate 1; 1.00 g, 6.8 mmol), 2-ethoxyphenylboronic acid (Combiblock; 1.12 g, 6.8 mmol), copper(II) acetate (1.24 g, 6.8 mmol) and triethylamine (960 μL, 6.8 mmol) in 1,2-dichloroethane (15 mL) was heated in an oil bath at 50° C. overnight. The mixture was allowed to cool, and it was then adsorbed onto silica gel and purified by chromatography using an ISCO 120 g column, eluting with 20-25% ethyl acetate/hexanes, to give N′-(2-ethoxy-phenyl)-N-methyl-hydrazinecarboxylic acid tert-butyl ester (751 mg, 38%) as an off-white solid.

Workup

  1. temperatureto cool
  2. custompurified by chromatography
  3. washeluting with 20-25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-42292a9fdc2d45ebacca33277c4cfcd7
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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