Potassium Bromide → HCID 59021636, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 18.0 g Boc-N-methyl-alaninol (95 mmol) in 95 ml dichloromethane was added a solution of 3.2 g NaHCO3 (38 mmol) and 1.14 g KBr (9.5 mmol) in 95 ml deionized water. The reaction mixture was cooled to 0° C. and after the addition of 152 mg 2,2,6,6-tetramethyl-piperidin-1-oxyl (TEMPO, 0.95 mmol), 72 g 10.3% aqueous sodium hypochlorite (105 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 38% aqueous sodium bisulfite (1 ml) and the reaction mixture was warmed up to 20°. The aqueous layer was extracted with 100 ml dichloromethane and the organic layers were washed with 100 ml 10% brine and dried (Na2SO4). Removal of the solvent by rotary evaporation afforded 14.4 g (80%) crude product as a light orange oil, [α]D=−82 (CHCl3; c=1). 1H-NMR:

Provenance & Evidence