Diethyl (cyanomethyl)phosphonate → Tert-butyl 3-(3-cyanoallyl)azetidine-1-carboxylate

To a solution of potassium tert-butoxide, 1M in tetrahydrofuran (3694 μl, 3.69 mmol) at 0° C. was added dropwise by syringe a solution of diethyl cyanomethylphosphonate (570 μl, 3.52 mmol) in 5 ml tetrahydrofuran. The reaction mixture was warmed to room temperature and then cooled to 0° C. again. This solution was treated with tert-butyl 3-(2-oxoethyl)azetidine-1-carboxylate (701 mg, 3.52 mmol) in 2 ml tetrahydrofuran dropwise by syringe and then allowed to warm to room temperature. After stirring overnight the gelatinous mixture was quenched with water (20 ml) and extracted with ethyl acetate (2×20 ml); the organic layers were washed with brine (20 ml), dried with magnesium sulfate, filtered and concentrated. The liquid residue was flash chromatographed to give the title compound as a 1:1 mixture of E/Z isomers.

1. temperaturecooled to 0° C. again
2. temperatureto warm to room temperature
3. customwas quenched with water (20 ml)
4. extractionextracted with ethyl acetate (2×20 ml)
5. washthe organic layers were washed with brine (20 ml)
6. dry with materialdried with magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customchromatographed

ORD record

ord-89dad198247d471b9271b2a515232c3b

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09302989B2