Methanol → (R)-1-Boc-2-azetidinemethanol

To a solution of 2M LiBH4 (200 ml, 400 mmol) in THF at 0° C. was added TMSCl (101 ml, 800 mmol) slowly. The mixture was warmed up to r.t and stirred at r.t. for 30 min. To the mixture at 0° C. was added a solution of (R)-1-(tert-butoxycarbonyl)azetidine-2-carboxylic acid (40 g, 200 mmol) in 200 ml THF with an additional funnel over 1 hour. The mixture was warmed up to r.t and stirred at r.t. for 2 hours. The mixture was cooled down to 0° C. and then treated with 32 mL MeOH followed by 40 mL H2O. After removal of THF, the residue was extracted with 300 mL EtOAc and washed with 300 mL brine. The organic layer was dried and concentrated to give (R)-tert-butyl 2-(hydroxymethyl)azetidine-1-carboxylate as a colorless oil (32.5 g, 87%). LRMS (M−100+H+) m/z 132.1.

1. temperatureThe mixture was warmed up
2. temperatureThe mixture was warmed up
3. stirringstirred at r.t. for 2 hours
4. temperatureThe mixture was cooled down to 0° C.
5. customAfter removal of THF
6. extractionthe residue was extracted with 300 mL EtOAc
7. washwashed with 300 mL brine
8. customThe organic layer was dried
9. concentrationconcentrated

ORD record

ord-bd5711ec17f04b53bd679a16766ce1d1

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07932270B2