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 (APCl) (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-683026977ad74c3582d1a6bb62307944

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07179934B2