Triethylamine → N-benzyl-N'-(2,3-dimethyl-phenyl)-hydrazinecarboxylic acid tert-butyl ester

HRID 1438065Notes

Reaction equation

HRID 1438065 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH2:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][C:18]1[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O.C(N(CC)CC)C>ClCCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH:9][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]([CH3:24])[C:18]=1[CH3:17])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27733952,3-Dimethylphenylboronic acidHCID 10799067N-benzyl(tert-butoxy)carbohydrazide2×

Product 1

HCID 57941521N-benzyl-N'-(2,3-dimethyl-phenyl)-hydrazinecarboxylic acid tert-butyl esterYield 39.6%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of N-benzyl-hydrazinecarboxylic acid tert-butyl ester (Intermediate 27; 790 mg, 3.55 mmol), 2,3-dimethylphenylboronic acid (Aldrich; 522 mg, 3.48 mmol), copper(II) acetate (646 mg, 3.55 mmol) and triethylamine (500 μL, 3.55 mmol) in 1,2-dichloroethane (5.5 mL) was heated in an oil bath at 50° C. for 2 h. The mixture was allowed to cool, and it was then adsorbed onto silica gel and purified by chromatography using an ISCO 40 g column, eluting with 20-40% ethyl acetate/hexanes, to give N-benzyl-N′-(2,3-dimethyl-phenyl)-hydrazinecarboxylic acid tert-butyl ester (450 mg, 39%) as a yellow oil.

Workup

  1. temperatureto cool
  2. custompurified by chromatography
  3. washeluting with 20-40% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-16503d8681624c049d9b7e2735ef3f49
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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