Isopropyl chloroformate → tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of 1-Boc-azetidine-3-carboxylic acid (1.6 g) and Et3N (2 mL) in anhydrous THF (60 mL) was cooled to 0° C. Isopropyl chloroformate (1.3 g) was added via a syringe slowly; forming a white precipitate almost immediately. The reaction was stirred for 1 h at 0° C. and the precipitate was filtered out. The filtrate was cooled to 0° C. again and aqueous NaBH4 solution (900 mg, 5 mL) was added via pipette and stirred for 1 h. The reaction was quenched with NaHCO3 solution (50 mL) and the product was extracted with EtOAc (200 mL). The organic phase was washed with brine (50 mL), dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in EtOAc and passed through a short silica gel pad. Concentrating the filtrate in vacuo provided the compound as a light yellow oil.

Provenance & Evidence