Hydrochloric Acid → tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylate

Borane dimethyl sulfide complex (4.5 mL, 15.0 mmol) was slowly added to 1-(tertiary butoxycarbonyl)azetidine-3-carboxylic acid (1.0 g, 5.0 mmol) dissolved in a distilled tetrahydrofuran solution (20 mL) at 0° C., and the mixture was stirred at the same temperature for 4 hours. Thereafter, 1N HCl aqueous solution (70 mL) was slowly added at 0° C., and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was extracted with ethyl acetate (3*30 mL), and the organic layer was washed with a saturated sodium chloride solution and distilled water once, respectively and dried over anhydrous magnesium sulfate. The solvent was removed by reduced pressure evaporation to obtain the desired compound tertiary butyl 3-(hydroxymethyl)azetidine-1-carboxylate.

1. stirringthe mixture was stirred at room temperature for 30 minutes
2. extractionThe reaction mixture was extracted with ethyl acetate (3*30 mL)
3. washthe organic layer was washed with a saturated sodium chloride solution
4. distillationdistilled water once
5. dry with materialrespectively and dried over anhydrous magnesium sulfate
6. customThe solvent was removed by reduced pressure evaporation

ORD record

ord-a08b0a51f8ba4e3c95fb4780f37a7b44

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09120771B2