Org Prep Daily

September 25, 2006

3-(N-morpholinemethyl)-oxetane-3-methanol

Filed under: procedures — milkshake @ 7:39 pm

2,2-Bis-(bromomethyl)-1,3-propanediol 131.0g (500mmol) and sodium methoxide 27.0g (500mmol) slurry in anhydrous ethanol 0.4L was stirred at 60C for 8 hours (overnight). The mixture was cooled, filtered (the salts were washed with ethanol) and the filtrates were concentrated on rotavap. The residue was distilled on Kugelrohr apparatus at 1 Torr (the air bath temperature was gradually increased from R.T. to 160C) to provide crude 3-bromomethyloxetane-3-methanol 69.0g (76.5%) as a colorless syrupy liquid.

This intermediate bromide was mixed with neat morpholine 130mL (1.5 mol) and the mixture was stirred at 60C for 20 hours. The mixture was cooled, diluted with TBME 100mL, the salts were removed by filtration (washed with additional TBME) and the filtrates were concentrated on rotavap. The residue was distilled on highvac using a shortpath distillation head. The pure product distilled at 125-135C/0.5Torr. Y=61.12g (85% from monobromide, 65% overall) of a colorless syrup.

1H(CDCl3, 400MHz): 4.976(br s, 1H), 4.480(d, 6.3Hz, 2H), 4.388(d, 6.3Hz, 2H), 4.055(s, 2H), 3.666(app br t, 4.7Hz, 4H), 2.819(s, 2H), 2.433(app br t, 4.7Hz, 4H); 13C(CDCl3, 100MHz): 78.01(2C), 69.08, 66.47(2C), 65.46, 54.16(2C), 42.23

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