Borane;tetrahydrofuran → HCID 67107599, compound

Participants

Reaction Steps

A solution of t-butyl 2-diethylcarbamoylazetidine-1-carboxylate (0.614 g) in THF (15 ml) was cooled in an ice/water bath and borane/THF complex (1M in THF, 7.68 ml) was added dropwise over 15 minutes. The mixture was then warmed to room temperature and stirred for a further 18 hours. The mixture was evaporated to dryness and ethanol and water (9:1, 20 ml) was added. The reaction mixture was then heated to reflux for 3 hours. After cooling, it was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of DCM:methanol:acetic acid:water with a gradient of 350:20:3:2 to 120:15:3:2 to give t-butyl 2-diethylaminomethylazetidine-1-carboxylate (0.47 g) as a yellow oil.

Provenance & Evidence