Water → tert-Butyl 3-cyano-3-methylazetidine-1-carboxylate

Temperature

-78 °C

tert-Butyl 3-cyanoazetidine-1-carboxylate (0.5 g, 2.74 mmol) was dissolved in 11 mL of THF and the reaction was cooled to −78° C. Sodium bis(trimethylsilyl)amide (3.02 mL of a 1M THF solution, 3.02 mmol) was added slowly. After 30 min, iodomethane (0.26 mL, 4.12 mmol) was added. The reaction mixture was stirred at −78° C. for 30 min then warmed to room temperature over 16 h. Water and ethyl acetate were added to the reaction, the layers were separated and the aqueous layer was extracted twice more with ethyl acetate. The combined organic layers were washed with sodium chloride solution, dried over magnesium sulfate, and evaporated. The residue was purified by silica gel chromatography (ethyl acetate/hexanes) to give 0.23 g (42%) 3-cyano-3-methyl-azetidine-1-carboxylic acid tert-butyl ester.

1. temperaturethen warmed to room temperature over 16 h
2. customthe layers were separated
3. extractionthe aqueous layer was extracted twice more with ethyl acetate
4. washThe combined organic layers were washed with sodium chloride solution
5. dry with materialdried over magnesium sulfate
6. customevaporated
7. customThe residue was purified by silica gel chromatography (ethyl acetate/hexanes)

ORD record

ord-4ac0433a2ddc4eb4be439f81eae154c9

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08518945B2