tert-Butylsulfinamide, (S)-(-)- → (S)-2-Methyl-propane-2-sulfinic Acid ((3S)-1,3-dimethyl-pentylidene)-amide

A mixture of (S)-4-methyl-hexan-2-one (1.6 g, 14 mmol), (S)-2-methyl-propane-2-sulfinic acid amide (1.7 g, 14 mmol) and titanium(IV) ethoxide (6.4 g, 28 mmol) in THF (30 mL) was refluxed for 10 hours. Then the reaction mixture was poured into brine (150 mL). The mixture was filtered. The filtrate was extracted by EtOAc (3×70 mL). The EtOAc phase was removed under reduce pressure and the residue was purified by a silica gel column (Hexane/EtOAc 3:1) to give the titled compound (1.93 g, 63% yield) as a colorless oil: 1H NMR (CDCl3) δ 2.24 (m, 2H), 2.27 (s, 3H), 1.85 (m, 1H), 1.22 (m, 2H), 1.20 (s, 9H), 0.85 (m, 6H); MS (APCI) (M+1)+ 218.1.

1. temperaturewas refluxed for 10 hours
2. filtrationThe mixture was filtered
3. extractionThe filtrate was extracted by EtOAc (3×70 mL)
4. customThe EtOAc phase was removed
5. customthe residue was purified by a silica gel column (Hexane/EtOAc 3:1)

ORD record

ord-b893801a673040d08b755176e997b607

Source dataset

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07388023B2