Potassium Bromide → HCID 11535949, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 37.0 g Boc-N-methyl-isoleucinol (160 mmol) in 160 ml dichloromethane was added a solution of 5.4 g NaHCO3 (64 mmol) and 1.9 g KBr (16 mmol) in 160 ml deionized water. The reaction mixture was cooled to 0° C. and after the addition of 125 mg 2,2,6,6-tetramethyl-piperidin-1-oxyl (TEMPO, 0.8 mmol), 122.6 g 10.2% aqueous sodium hypochlorite (176 mmol Cl2) were added under stirring over 2.5 h at 0-5°. After additional stirring for 30 min the excess of NaOCl was destroyed by the addition of ca. 1 ml 38% aqueous sodium bisulfite and the reaction mixture was warmed up to 20°. The aqueous layer was extracted with 160 ml dichloromethane and the organic layers were washed with 10% brine and dried (Na2SO4). Removal of the solvent by rotary evaporation afforded 35.7 g (97.2%) crude product as a light orange oil.

Provenance & Evidence