Acetic Acid → HCID 86671315, compound

Participants

Reaction Steps

To a solution of 6-bromopyridine-2-carbaldehyde (5.00 g, 26.9 mmol) in methanol (75 mL) at ambient temperature was added D-valinol (3.00 mL, 26.9 mmol) followed by acetic acid (6.2 mL, 110 mmol). After 5 minutes, MP-cyanoborohydride (2.49 mmol/g; 12 g) was added and stirred overnight. The mixture was filtered, concentrated. The residue was partitioned between 1N NaOH and CH2Cl2. The organic phase was dried (Na2SO4) and concentrated. The residue was purified by chromatography (50% ethyl acetate:CH2Cl2 to remove non polar impurites, then ethyl acetate to 20% acetone:ethyl acetate) to provide 4.39 g (60%) of the title compound. MS (DCI30 ) m/z 273/275 (M+H).

Provenance & Evidence