(NE,S)-2-methyl-N-(oxetan-3-ylmethylidene)propane-2-sulfinamide → (S)-2-methyl-propane-2-sulfinic acid ((R)-1-oxetan-3-yl-ethyl)-amide

Temperature

-76 °C

In a round-bottomed flask, (S)-2-methyl-propane-2-sulfinic acid 1-oxetan-3-yl-meth-(E)-ylideneamide (172 mg, 0.91 mmol) was dissolved in dichloromethane (3.6 ml). The colorless solution was cooled to −76° C. and methylmagnesium bromide (3.0 M in diethyl ether, 0.91 ml, 2.73 mmol) was added dropwise. The reaction mixture was stirred at −76° C. for 3 h and then allowed to warm slowly to room temperature overnight. The reaction was quenched with saturated NH4Cl-solution then extracted with EtOAc (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated to provide 143 mg (77%) of (S)-2-methyl-propane-2-sulfinic acid ((R)-1-oxetan-3-yl-ethyl)-amide as a light yellow oil which was used without further purification.

1. temperatureto warm slowly to room temperature overnight
2. customThe reaction was quenched with saturated NH4Cl-solution
3. extractionthen extracted with EtOAc (2×)
4. washThe combined organic layers were washed with water and brine
5. dry with materialthen dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-7638b1a6d98348559483e747048f0fe4

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658646B2