Methanol → HCID 66594849, compound

Participants

Reaction Steps

A solution of (6S)-4-benzyl-6-(5-bromo-2-methoxyphenyl)-morpholin-3-one (67.2 g, 179 mmol) in tetrahydrofuran (200 ml) was added to an ice-cooled mixture of lithium borohydride (8.55 g, 393 mmol) and chlorotrimethylsilane (99.7 ml, 785 mmol) in tetrahydrofuran (500 ml) over 45 minutes and the solution was stirred at same temperature for one hour and then at room temperature for 5 hours. After careful addition of methanol (60 ml) to the ice-cooled solution, solvent was removed under reduced pressure and the residue in 10% aqueous sodium hydroxide (280 ml) was stirred at 90° C. for 3 hours. The solvents were removed under reduced pressure and the residue was partitioned between water and diethyl ether. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification of the residue by silica gel column chromatography (hexane/ethyl acetate) gave (2S)-4-benzyl-2-(5-bromo-2-methoxyphenyl)-morpholine (46.1 g, 71%, 2 steps) as a yellow oil.

Provenance & Evidence