Hydrogen Peroxide → HCID 57467373, compound

HRID 510562Notes

Reaction equation

HRID 510562 reaction equation
CSC.[Cl:4][C:5]1[CH:6]=[C:7]([CH:27]=[CH:28][CH:29]=1)[CH2:8][CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH:19]=[CH2:20])[CH:17]=2)[CH2:12][CH2:11][CH:10]1[NH:21][C:22](=[O:26])[O:23][CH2:24][CH3:25].[OH:30]O.[OH-].[Na+]>C1COCC1.O>[CH2:24]([O:23][C:22](=[O:26])[NH:21][CH:10]1[CH2:11][CH2:12][C:13]2[C:18](=[CH:17][C:16]([CH2:19][CH2:20][OH:30])=[CH:15][CH:14]=2)[CH:9]1[CH2:8][C:7]1[CH:27]=[CH:28][CH:29]=[C:5]([Cl:4])[CH:6]=1)[CH3:25]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 1068Dimethyl SulfideHCID 14798Sodium HydroxideHCID 57471469HCID 57471469, compound

Product 1

HCID 57467373HCID 57467373, compoundYield 104.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

BH3.DMS (1 M in THF, 0.838 ml, 0.838 mmol) was added a solution of ethyl 1-(3-chlorobenzyl)-7-vinyl-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate (1.55 g, 4.19 mmol) in 20 ml dry THF. The reaction was stirred at 60° C. for 1 h and cooled to room temperature. Some water was added to destroy the excess of borane complex and the resulting mixture refluxed for 1 h with 30% H2O2 (8.56 ml, 84 mmol) and 2N NaOH (9.74 ml, 19.49 mmol). The reaction mixture was extracted with CH2Cl2, washed with water and brine, dried, filtered and the solvent evaporated to obtain a pale brown solid (1.7 g), which was purified by chromatography to afford 854 mg of product as a white solid.

Workup

  1. temperaturecooled to room temperature
  2. customto destroy the excess of borane complex
  3. extractionThe reaction mixture was extracted with CH2Cl2
  4. washwashed with water and brine
  5. customdried
  6. filtrationfiltered
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-53fc8dd5a6244dbdb53b0c0f90e537f8
Source dataset
uspto-grants-2015_08
Patent number
US09096619B2

Reaction notes

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