Morpholine → HCID 16641101, compound

Participants

Reaction Steps

Morpholine (1.19 mL, 13.7 mmol) was added to a solution of 2-bromo-5-hydroxybenzaldehyde (2.5 g, 12.4 mmol) in DCM (20 mL) and stirred for 20 min. Sodium triacetoxyborohydride (2.90 g, 13.7 mmol) was added and stirred for 2 h. The reaction was quenched with methanol and stirred for 1 h. The solution was concentrated in vacuo, dissolved in methanol and loaded onto a SCX (50 g) column, flushing with methanol. Eluting with methanolic ammonia and concentration of the eluant gave the 4-bromo-3-(morpholinomethyl)phenol (3 g, 11.02 mmol), which was dissolved in THF (60 mL) cooled to −78° C. and tert-butyllithium (19.45 mL, 33.07 mmol) (1.7M) was added dropwise. The reaction mixture stirred for 10 min then warmed to 0° C. for 15 min. The reaction was then cooled to −78° C. and triisopropyl borate (7.63 mL, 33.07 mmol) was added. The reaction was warmed to RT and stirred for 1 hr. Saturated aqueous ammonium hydroxide was added and the reaction stirred at RT for 2 h. The reaction mixture was diluted with EtOAc (200 mL), the phases were separated, the aqueous was further extracted with EtOAc. The combined organic extracts were washed with saturated brine (200 mL). The organic was dried over magnesium sulfate, filtered and evaporated to give the sub-title compound. Yield: 2.45 g

Provenance & Evidence