4-Phenoxybenzaldehyde → (S)-4-(4-phenoxybenzyl)-2-phenylmorpholine

Participants

Reaction Steps

200 mg of (S)-2-Phenyl-morpholine (see synthesis in Example 1) was dissolved in 2 mL of dichloroethane and 253 μL of 4-Phenoxy-benzaldehyde was added. The reaction was stirred at room temperature 30 minutes and then 467 mg of sodium triacetoxyborohydride was added. The reaction was stirred overnight at room temperature. The reaction solution was then washed with aqueous saturated sodium bicarbonate solution several times followed by a brine wash. The organics were dried over sodium sulfate, filtered and concentrated in vacuo. Purification by preparatory chromatography gave the title compound. 8% yield. EI m/z 346=MH+

Provenance & Evidence