Sodium Hydroxide → HCID 86673443, compound

Temperature

0 °C

To tert-butyl carbamate (214 mg, 1.827 mmol) in n-propanol (1.75 mL) was added sodium hydroxide (71.3 mg, 1.784 mmol) in water (3.5 mL) followed by tert-butyl hypochlorite (0.201 mL, 1.78 mmol). After 5 min, the solution was cooled to 0° C. and treated with a solution of DHQD2(PHAL) (23.7 mg, 0.030 mmol) in n-propanol (1.75 mL). The reaction was diluted with n-propanol (3.5 mL), and treated with (E)-6-bromo-3-fluoro-2-styrylpyridine (121 mg, 0.435 mmol) as a solid in one portion. To this was added potassium osmate dihydrate (8.01 mg, 0.022 mmol) as a solid in one portion. The reaction was allowed to gradually warm to room temperature in the dewar overnight. The reaction was cooled to 0° C. and quenched by addition of sodium thiosulfate (150 mg) in water (3 mL). The ice bath was removed and stirring continued for 30 min. The reaction was diluted with ether, washed with water (3×), then brine, dried over magnesium sulfate, and concentrated. Column chromatography (25% EtOAc/Hex) gave 208 mg (quant.). Mass spec.: 411.1 (MH)+.

1. temperatureto gradually warm to room temperature in the dewar overnight
2. temperatureThe reaction was cooled to 0° C.
3. customquenched by addition of sodium thiosulfate (150 mg) in water (3 mL)
4. customThe ice bath was removed
5. waitcontinued for 30 min
6. additionThe reaction was diluted with ether
7. washwashed with water (3×)
8. dry with materialbrine, dried over magnesium sulfate
9. concentrationconcentrated
10. customColumn chromatography (25% EtOAc/Hex) gave 208 mg (quant.)

ORD record

ord-57b4c05cbdbf49b1b07d3f4214f97463

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691821B2