Hydrochloric Acid → HCID 54670055, compound

Participants

Reaction Conditions

Reaction Steps

A second reaction vessel was charged with MeOH (2 mL), cooled to −78° C. using a dry-ice/acetone cooling bath, and treated with sodium cyanoborohydride (0.105 g, 1.673 mmol), followed by the dropwise addition of HCl (1.339 mL, 1.673 mmol, 1.25 M in MeOH). After stirring at −78° C. for approximately 5 min, the material from Step A was added portion wise over approximately 15 min. The reaction was gradually warmed to rt and aged for 12 h. A solution of aq. 5 M NaOH was added until the pH of the reaction mixture was basic. The biphasic mixture was filtered through a plug of Celite™ while rinsing with EtOAc. The organic layer of the filtrate was separated and washed with saturated aq. NaCl, dried (Na2SO4), filtered and concentrated. The resulting residue was purified by flash chromatography on silica gel via gradient elution with 0-50% EtOH/EtOAc. The purified fractions were combined and concentrated to afford the faster eluting isomer (at * carbon) as Example 3 [HPLC/MS: 509.3 (M+1); Rt=2.85 min] and the slower eluting isomer (at * carbon) as Example 4 [HPLC/MS: 509.3 (M+1); Rt=2.83 min].

Provenance & Evidence