Chlorotrimethylsilane → HCID 59924243, compound

Temperature

-78 °C

To a solution of (2R)-2-amino-2-phenylethanol (960 mg) in methylene chloride (30 ml) was added triethylamine (2.0 ml) and the mixture was cooled to −78° C. To the mixture was added dropwise chlorotrimethylsilane (0.90 ml), the mixture was stirred for 3 hours at −78° C. and then stirred for 1 hour at 0° C. The reaction mixture was cooled to −78° C. again. To the mixture was added dropwise 1-octanesulfonyl chloride (1.4 ml) and the mixture was stirred for 2 hours at −78° C. and then stirred for 15 hours at 0° C. The reaction mixture was diluted with ethyl acetate and then washed with 1N hydrochloric acid, a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1→3:2) to give the title compound (1.70 g) having the following physical data.

1. stirringstirred for 1 hour at 0° C
2. temperatureThe reaction mixture was cooled to −78° C. again
3. stirringthe mixture was stirred for 2 hours at −78° C.
4. stirringstirred for 15 hours at 0° C
5. washwashed with 1N hydrochloric acid
6. dry with materiala saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate
7. concentrationconcentrated
8. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1→3:2)

ORD record

ord-7993583675514f20b7310f9b96be723b

Source dataset

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06495533B1