Sodium Hydroxide → HCID 70957274, compound

Participants

Reaction Conditions

Reaction Steps

To tert-butyl carbamate (1256 mg, 10.73 mmol) in propanol (25 mL) was added sodium hydroxide (422 mg, 10.55 mmol) in water (30 mL) followed by tert-butyl hypochlorite (1.191 mL, 10.55 mmol). The solution was cooled to 0° C. and (DHQD)2PHAL (67.4 mg, 0.086 mmol) and (DHQ)2PHAL (67.4 mg, 0.086 mmol) were added in propanol (20 mL) followed by (E)-3-(3-bromostyryl)pyridine (900 mg, 3.46 mmol) in propanol (25 mL) and finally potassium osmate dihydrate (51.0 mg, 0.138 mmol) in one portion. The mixture was allowed to stir overnight and come to ambient temperature in the process. The mixture was quenched with sodium sulfite (50 mL) and the mixture was extracted with 3×50 mL ethyl acetate and the combined organics were washed with sodium sulfite (25 mL) and brine (25 mL), dried over MgSO4, filtered and concentrated to an amber oil which was loaded with dichloromethane onto a 90 g silica gel cartridge pre-equilibrated with 5% ethyl acetate/hexanes. Elution with 5 to 100% ethyl acetate over 2.5 L provided 965 mg (71%) as a mixture of regioisomers. LC/MS (analytical HPLC method 1; 1.63 min): Anal. Calcd. for [M+H]+ C18H21BrN2O3: 393.07. found 392.97.

Provenance & Evidence