Boron Trichloride → HCID 86686872, compound

Participants

Reaction Conditions

Reaction Steps

The crude intermediate 4-((1R,3S,4S)-3-(benzyloxy)-4-(benzyloxymethyl)cyclopentyloxy)-6-chloropyrimidine (25) was taken up in methylene chloride (3000 mL) and the mixture was cooled to 0° C. 1.0 M of Trichloro-borane in methylene chloride (1087.538 mL, 1087.538 mmol) was added slowly maintaining <10° C. The resulting mixture was allowed to stir for 1 hour at 0° C. HPLC analysis indicated consumption of starting material. The reaction mixture was added slowly to saturated sodium bicarbonate in water (2300 mL) and the biphasic mixture was allowed to stir for 20 minutes. The methylene chloride layer was separated and the aqueous extracted twice with methylene chloride (2300 mL). The organics were combined and concentrated. The residue was purified by eluting through a silica gel (1 kg) plug with 50 to 100% ethyl acetate/hexane (hexane (6 L)+ethyl acetate (14 L). The desired fractions were combined and concentrated to give a red solid (124 g, 70%). 1H NMR (300 MHz, CD3OD, δ): 8.58 (s, 1H), 6.91 (s, 1H), 5.61 (m, 1H), 4.39 (t, 1H), 3.75 (m, 1H), 3.61 (m, 1H), 2.25 (m, 3H) and 2.00 (m, 2H)

Provenance & Evidence