Hydrogen Peroxide → HCID 59226061, compound

Participants

Reaction Steps

2.87 mL (1.43 mmol) of a 0.5M solution of 9-BBN in THF were added to a solution of 250 mg (0.48 mmol) of [1-allyl-4-(1-benzyloxy-7-chloro-isoquinolin-6-yloxy)-cyclohexyl]-carbamic acid tert-butyl ester (52) in 5 mL THF at 0° C. The reaction mixture was allowed to warm to room temperature over night, before being cooled to 0° C. Then, 5 mL of 3M aqueous sodium hydroxide and 5 mL of 30% aqueous hydrogen peroxide were added slowly, and the mixture was stirred for 5 h. The mixture was extracted twice with ethyl acetate, washed with water and saturated sodium chloride solution, dried over magnesium sulfate and concentrated in vacuo. 196 mg of the title compound 53 could be isolated as mixture of diastereoisomers in a purity sufficient for further conversion. Rt=2.05 min (Method C). Detected mass: 541.3 (M+H+).

Provenance & Evidence