Hydrochloric Acid → HCID 54670055, compound

Participants

Reaction Conditions

Reaction Steps

A second reaction vessel was charged with MeOH (5 mL), cooled to −78° C. and sodium cyanoborohydride (0.261 g, 4.16 mmol) was added, followed by drop-wise addition of HCl (3.33 mL, 4.16 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 warmed to rt over about 12 h, then 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™, which was rinsed 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 0-20% EtOH/EtOAc. The purified fractions were combined and concentrated to afford the faster eluting isomer (at * carbon) as Example 1 [HPLC/MS: 509.3 (M+1); Rt=2.85 min] and the slower eluting isomer (at * carbon) as Example 2 [HPLC/MS: 509.3 (M+1); Rt=2.80 min].

Provenance & Evidence