tert-Butyl acetate → Tert-butyl 3-(tert-butylsulfinylamino)-3-cyclopropyl-butanoate

Temperature

-78 °C

To a solution of tert-butyl acetate (1.29 g, 1.48 ml, 11.1 mmol) in THF (20 ml) cooled to −78° C. was added a 2M solution of lithium diisopropylamine in THF/n-heptane (5.55 ml, 11.1 mmol) over 10 minutes. The reaction mixture was stirred for 40 minutes at −78° C. followed by addition of a solution of (E)-N-(1-cyclopropylethylidene)-2-methylpropane-2-sulfinamide (CAN 1426425-10-6, 1.6 g, 8.54 mmol) in THF (5 ml) to the reaction cooled at −78° C. The reaction was stirred at −78° C. for 90 minutes and then let to warm up to 0° C. After stirring 1 hour at 0° C. the reaction was quenched by addition of water. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic phase was dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient to yield the title compound (1.93 g, 75%). MS (ESI, m/z): 304.5 (M+H+).

1. temperaturecooled at −78° C
2. stirringThe reaction was stirred at −78° C. for 90 minutes
3. temperatureto warm up to 0° C
4. stirringAfter stirring 1 hour at 0° C. the reaction
5. customwas quenched by addition of water
6. additionThe reaction mixture was diluted with ethyl acetate
7. washwashed with brine
8. dry with materialThe organic phase was dried over sodium sulfate
9. customevaporated down to dryness
10. customThe crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient

ORD record

ord-8f5c0810ef8a4b94a7d24f16ae1a89b5

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409866B2