tert-Butyl carbazate → N'-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexylidene]-hydrazinecarboxylic acid tert-butyl ester

HRID 12888Notes

Reaction equation

HRID 12888 reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:16]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:19])[NH:17][NH2:18]>>[C:21]([O:20][C:16]([NH:17][N:18]=[C:12]1[CH2:13][CH2:14][CH:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:10][CH2:11]1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

3

Reactant 2

HCID 70091tert-Butyl carbazateHCID 111955462-(tert-Butyldimethylsilyloxy)cyclohexanone

Product 1

HCID 67020959N'-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexylidene]-hydrazinecarboxylic acid tert-butyl esterYield 90.1%

Conditions

Temperature
70 °C

Procedure

tert-Butyldimethylsilyloxy-cyclohexanone (3.146 g, 97%, 13.36 mmol, CAS #55145-45-4, purchased from Aldrich) was dissolved in hexanes (24 mL). tert-Butyl carbazate (1.80 g, 98%, 13.35 mmol) was added and the mixture was heated at 70° C. for 3 hours. Upon cooling to room temperature a white solid precipitated out of solution. The solid was collected by filtration, washed with hexanes and dried to give N′-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-hydrazinecarboxylic acid tert-butyl ester (4.12 g, 90%).

Workup

  1. temperatureUpon cooling to room temperature a white solid
  2. customprecipitated out of solution
  3. filtrationThe solid was collected by filtration
  4. washwashed with hexanes
  5. customdried

Sources & evidence

ORD record
ord-340ad6098b5640589aae7bb301b76e43
Source dataset
uspto-grants-2010_06
Patent number
US07728029B2

Reaction notes

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