Sodium borohydride → 1-(Isoquinolin-1-yl)ethan-1-ol

Participants

Reaction Conditions

Reaction Steps

1-Acetyl-isoquinoline (2.0 g, 11.7 mmole) is dissolved in 50 ml methanol in a 100 ml one neck round bottom flask at 0° C. The solution is treated portionwise with sodium borohydride (495 mg, 13.1 mmole) and the reaction mixture is stirred for 1 h at 0° C. The volatiles are removed in vacuo and the residue is partitioned between 1×50 ml 1N sodium hydroxide and 4×25 ml dichloromethane. The combined organics are dried over potassium carbonate and are concentrated in vacuo to a pale oil. The crude material is chromatographed over 100 g silica gel (230-400 mesh), eluting with 15% acetone/hexane, while collecting 22 ml fractions. Fractions 23-37 are combined and concentrated to afford 1.99 g (98%) of 1-(1-hydroxyethyl)-isoquinoline.

Provenance & Evidence