Sodium Hydroxide → (R)-(5-Bromo-1,2,3,4-tetrahydroisoquinolin-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

Add lithium aluminum hydride (2 L, 2.00 mol, 1M in THF) to (3R)-5-bromo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride (325.4 g, 1.11 mol) in tetrahydrofuran (4.88 L) at −35° C. in an appropriate vessel, then warm to 25° C. over 60 minutes and stir. After 3 hours, cool the mixture to −5° C. then add water (76 mL), 15% w/w aqueous sodium hydroxide (76 mL) and water (228 mL). Heat the mixture to 25° C., add anhydrous magnesium sulfate (750 g) and stir. Filter the mixture and concentrate under reduced pressure to give a solid. Add dichloromethane (690 mL) to the solid and slurry for 30 minutes before filtration to give a solid. Dry the solid under vacuum at 35° C. to give the title compound (148.9 g, 0.55 mol). MS (m/z): 242(M+1 (79Br)), 244(M+1 (81Br)).

Provenance & Evidence