Formaldehyde → HCID 57816716, compound

Temperature

-78 °C

To a solution of tert-butyl cyclopropylsulfonylcarbamate (30 g, 136 mmol) in 750 mL of THF was added dropwise butyllithium (1.6 M in hexane, 212 mL, 339 mmol) over 30 min at −78° C. and the resulting mixture was stirred at −78° C. for 1 h. Formaldehyde gas was generated from para-formaldehyde (by heating at 180° C.) and was purged into the above reaction mass for 30 min at −30° C. The reaction was stirred at the same temperature for 1 h, then allowed to warm to room temperature. The reaction was quenched with aqueous ammonium chloride solution and diluted with water. The resulting mass was washed with ethyl acetate and the aqueous layer was acidified to pH˜2 and extracted with ethyl acetate. The combined organics were dried over sodium sulfate, filtered and evaporated under reduced pressure to get desired compound (27 g, 79%) as white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 10.90 (sb, 1H), 4.95 (sb, 1H), 3.75 (s, 2H), 1.42 (s, 9H), 1.27 (m, 2H), 1.08 (m, 2H).

1. customwas purged into the above reaction mass for 30 min at −30° C
2. stirringThe reaction was stirred at the same temperature for 1 h
3. temperatureto warm to room temperature
4. customThe reaction was quenched with aqueous ammonium chloride solution
5. additiondiluted with water
6. washThe resulting mass was washed with ethyl acetate
7. extractionextracted with ethyl acetate
8. dry with materialThe combined organics were dried over sodium sulfate
9. filtrationfiltered
10. customevaporated under reduced pressure

ORD record

ord-53421a8bc45a4e2d988d0a8ef7e38534

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691757B2