Sodium borohydride → HCID 18635825, compound

Participants

Reaction Steps

A solution of 149 mg of 3'-O-acetyl-5'-[3-(2,6-dichlorophenyl)-2-oxopropyl]-2',5'-dideoxy-5-ethyluridine and 26 mg of sodium borohydride in 7 ml of dimethoxyethane was stirred at room temperature for 2.5 hours. The solvent was removed by evaporation and the residue was taken up in 22 ml of 5% ammonium chloride solution and extracted twice with 20 ml of ethyl acetate each time. The extracts were washed with 20 ml of water, dried over anhydrous sodium sulphate and evaporated to give 3'-O-acetyl-5'-[3-(2,6-dichlorophenyl)-2(RS)-hydroxypropyl]-2',5'-dideoxy-5-ethyluridine in the form of a colourless gum. This was dissolved in 3 ml of 0.1M sodium methoxide solution and stirred at room temperature for 1 hour. The solution was then diluted with 150 ml of methanol, stirred with a cross-linked polystyrene/divinyl benzene cation exchange resin containing sulphonic acid groups (H+ form) and then filtered. The filtrate was evaporated and the residue was crystallized from ethanol to give 45 mg of 5'-[3-(2,6-dichlorophenyl)-2(RS)-hydroxypropyl]-2' ,5'-dideoxy-5-ethyluridine, mp 185°-186° C.

Provenance & Evidence