Hydrochloric Acid → HCID 53715070, compound

Participants

Reaction Steps

Methyl chloroformate (150 pL, 1.95 mmol) was added dropwise to a solution of 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-2-ethyl-malonic acid monoethyl ester (700 mg, 1.91 mmol) and Et3N (275 μL, 1.97 mmol) in THF (15 mL) at −20° C. under nitrogen. The reaction mixture was stirred for 50 min., filtered and added dropwise to a suspension of NaBH4 (80 mg, 2.1 mmol) in THF (15 mL) at −20° C. The reaction was stirred for 16 h at room temperature. 0.2 M HCl was added followed by methylene chloride. The organic phase was washed with brine and dried. Concentration under reduced pressure followed by chromathography (toluene/EtOAc, 3:1→1:3) gave 2-(6-tert-butoxycarbonylamino pyridin-3-ylmethyl)-2-hydroxymethyl-butyric acid ethyl ester (300 mg, 45%).

Provenance & Evidence