Aluminium lithium hydride → Tert-butyl 3-formylazetidine-1-carboxylate

Temperature

-70 °C

To a solution tert-butyl 3-{[methoxy(methyl)amino]carbonyl}azetidine-1-carboxylate (93.8 g, 0.3 mol) in tetrahydrofuran at −70° C. was added dropwise lithium aluminum hydride (12.3 g in 320 ml THF). After the addition was complete, the reaction mixture was stirred for 1 h at −70° C. The reaction was quenched by the addition of 13 ml of water, followed by 39 ml of 1N aqueous NaOH solution and 13 ml of water. The mixture was stirred for 1 h, filtered and concentrated. The residue was partitioned between 300 ml of ethyl acetate and 100 ml of water. The layers were separated and the organic layers were washed with 100 ml of brine. The organic layer was dried over magnesium sulfate, filtered and concentrated to afford tert-butyl 3-formylazetidine-1-carboxylate, which was used without additional purification.

1. additionAfter the addition
2. customThe reaction was quenched by the addition of 13 ml of water
3. stirringThe mixture was stirred for 1 h
4. filtrationfiltered
5. concentrationconcentrated
6. customThe residue was partitioned between 300 ml of ethyl acetate and 100 ml of water
7. customThe layers were separated
8. washthe organic layers were washed with 100 ml of brine
9. dry with materialThe organic layer was dried over magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated

ORD record

ord-ab89088071314319817a2361aea43062

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455477B2