Phosphate → [2-(4-Chloro-phenyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester

Temperature

0 °C

To a stirred solution of carbamic acid tert-butyl ester (0.22 g) in acetonitrile (6 mL) was added in sequence at 0° C.: Sodium hydroxide (52 mg) in water (5 mL); after 2 minutes tert-butyl hypochlorite (139 μL); after 10 minutes potassium osmate (V1) dihydrate (9 mg) in water (1 mL); after 1 minute hydroquinine (anthraquinone-1,4-diyl)diether (26 mg) in acetonitrile (4 mL); after 3 minutes acetonitrile (6.7 mL) and phosphate buffer (3.3 mL, 0.5 M pH 7.65); after 5 minutes enough sodium biphosphate monohydrate to make pH=7.65; and finally 4-fluorostyrene. The reaction was quenched after stirring 3 hours at 25° C. with sodium sulfite (0.20 g) in water (2 mL) at 0° C. The phases were separated and the aqueous layer extracted with ethyl acetate (3×20 mL). The combined organic phases were washed with water (1×50 mL), dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography to furnish 90 mg (57%) of the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3): 1.45 (s, 9H), 3.18 (m, 1H), 3.23 (m, 1H), 3.44 (m, 1H), 4.83 (m, 1H), 4.92 (b, 1H), 7.04 (t, 2H), 7.34 (m, 2H).

1. customThe reaction was quenched
2. customThe phases were separated
3. extractionthe aqueous layer extracted with ethyl acetate (3×20 mL)
4. washThe combined organic phases were washed with water (1×50 mL)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated in vacuo
7. custompurified by flash chromatography

ORD record

ord-8d475dd3b7564bda87d5b5746506f7b3

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07632835B2