Dimethyl Sulfide → HCID 178468164, compound

Temperature

50 °C

A flame dried 250 mL flask was charged with 7.95 g (27.5 mmol) trans-(4-acetyl-cyclohexylmethyl)-carbamic acid benzyl ester, 60 mL anhydrous THF and 2.7 mL (2.7 mmol) 1M (S)-2-methyl-CBS-oxazoborolidine. The mixture was heated to 50° C. then 11 mL (22 mmol) 2M BH3.DMS was added dropwise over 10 minutes; the reaction mixture was stirred for an additional 30 minutes at 50° C. and then cooled. The reaction was quenched with 25 mL MeOH and concentrated to give an oil. The material was diluted with water and extracted with ethyl acetate (3×40 mL). The combined organics were washed with water (1×100 mL), brine (1×100 mL), dried over Na2SO4 and concentrated to give a white solid, which was then chromatographed on silica gel eluted with 50% ethyl acetate/50% hexanes to give 7.0 g of a white solid.

1. customA flame dried 250 mL flask
2. temperaturecooled
3. customThe reaction was quenched with 25 mL MeOH
4. concentrationconcentrated
5. customto give an oil
6. extractionextracted with ethyl acetate (3×40 mL)
7. washThe combined organics were washed with water (1×100 mL), brine (1×100 mL)
8. dry with materialdried over Na2SO4
9. concentrationconcentrated
10. customto give a white solid, which
11. customwas then chromatographed on silica gel
12. washeluted with 50% ethyl acetate/50% hexanes

ORD record

ord-c61da89f16f14090941e0c060d6132d6

Source dataset

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06559168B2