Triethylamine → N-cyclopropyl-N'-phenyl-hydrazinecarboxylic acid tert-butyl ester

HRID 1437972Notes

Reaction equation

HRID 1437972 reaction equation
[C:1]([O:5][C:6]([N:8]([CH:10]1[CH2:12][CH2:11]1)[NH2:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>ClCCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]([CH:10]1[CH2:11][CH2:12]1)[NH:9][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 55296944tert-Butyl 1-cyclopropylhydrazinecarboxylate2×

Product 1

HCID 57941480N-cyclopropyl-N'-phenyl-hydrazinecarboxylic acid tert-butyl esterYield 45.3%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of N-cyclopropyl-hydrazinecarboxylic acid tert-butyl ester (Intermediate 28; 0.111 g, 0.64 mmol), phenylboronic acid (Aldrich; 156 mg, 1.3 mmol), copper(II) acetate (116 mg, 0.64 mmol) and triethylamine (180 μL, 1.3 mmol) in 1,2-dichloroethane (3 mL) was heated in an oil bath at 50° C. for 16 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 5-40% ethyl acetate/hexanes, to give N-cyclopropyl-N′-phenyl-hydrazinecarboxylic acid tert-butyl ester (72 mg, 45%) as a pale yellow solid.

Workup

  1. temperatureto cool
  2. custompurified by chromatography
  3. washeluting with 5-40% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-acf81872629140a6a47bcf76261b801f
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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