2-Bromopropane → HCID 15933238, compound

Temperature

90 °C

To a solution of tert-butyl thiol XXIIa(i) (1.50 mL, 13.2 mmol) in DMSO (8 mL) was added NaOMe (802 mg, 14.7 mmol) and isopropylbromide (0.62 mL, 6.54 mmol) at rt. The resulting cloudy solution was heated to 90° C. and stirred for 5 hrs at the same temperature. The reaction was quenched with water, extracted by ether, dried over MgSO4. The organic phase was concentrated to afford the crude sulfide. This sulfide was directly used for the next step. To a solution of the above crude sulfide in MeOH (30 mL) was added a solution of oxone (6.8 g, 11.0 mmol) in water (30 mL) at 0° C. The resulting cloudy solution was warmed to rt, then stirred for 5 hrs. The reaction mixture was concentrated using rotary evaporator, diluted with water, extracted with EtOAc. The organic layer was separated, dried over MgSO4, concentrated to afford the crude sulfone which was purified by flash chromatography (EtOAc:Hex=1:3 to 1:2) to give 594 mg (56% for 2 steps) of tert-butyl isopropyl sulfone XXIc(i)). Rf 0.36 (1:2-EtOAc:Hex); 1H NMR (400 MHz, CDCl3) δ 3.40 (m, 1H), 1.44 (s, 9H), 1.42 (d, J=6.8 Hz, 6H).

1. customThe reaction was quenched with water
2. extractionextracted by ether
3. dry with materialdried over MgSO4
4. concentrationThe organic phase was concentrated
5. customto afford the crude sulfide
6. temperatureThe resulting cloudy solution was warmed to rt
7. stirringstirred for 5 hrs
8. concentrationThe reaction mixture was concentrated
9. customevaporator
10. additiondiluted with water
11. extractionextracted with EtOAc
12. customThe organic layer was separated
13. dry with materialdried over MgSO4
14. concentrationconcentrated
15. customto afford the crude sulfone which
16. customwas purified by flash chromatography (EtOAc:Hex=1:3 to 1:2)

ORD record

ord-78be19ed2b144e74a2b2ef7db06469cd

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08106035B2