Water → HCID 86602704, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of triphenylphosphine (10.2 g), diethyl azodicarboxylate (6.12 ml), and (2S)-1-[N-benzyl-N-[(2S)-2-hydroxy-3-methoxypropyl]amino]-3-methoxypropan-2-ol (7.34 g) in tetrahydrofuran (70 ml) was stirred at 0° C. for 5 hours. To the mixture was added successively triphenylphosphine (2.04 g) and diethyl azodicarboxylate (1.2 ml), and the mixture was stirred at 0° C. for 3 hours. The mixture was poured into water and extracted with dichloromethane (×3). The combined extracts were washed with brine, dried over sodium sulfate, and evaporated. Isopropyl ether (50 ml) was added to the residue and stirred at room temperature for 30 minutes. The insoluble precipitate was filtered off, and the solution was evaporated and purified twice with column chromatography (1st: silica gel 800 ml, ethyl acetate:isopropyl ether=2:8–3:7) (2nd: silica gel 300 ml, ethyl acetate:isopropyl ether 3:97–10.90) to give 4-benzyl-cis-2,6-dimethoxymethylmorpholine (2.65 g) as an oil.

Provenance & Evidence