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(a) (3R)-Morpholin-3-ylmethanol; A solution of [(3i?)-4-benzylmorpholin-3-yl]methanol (see J. Med. Chem.; 29; 1986; 1288- 1290; 1.1 g, 5.4 mmol) in ethanol (25 mL) was mixed with palladium hydroxide (20% on carbon, 0.7 g) and acetic acid (0.5 mL). The mixture was stirred under hydrogen overnight20 at 1.2 bar and RT. The catalyst was filtered off and the solvent was removed by evaporation. The residue (except 200 mg) was dissolved in ether (1 mL) and THF (10 mL). The solution was filtered through a strong cation exchange column (Isolute SCX-2, 10 g). The column was washed with THF and then the product was eluted with ammonia- saturated methanol. The solvent was removed by evaporation and there was obtained 0.3625 g (57%) of (3i?)-morpholin-3-ylmethanol as an oil. 1H NMR (500 MHz, CD3OD): 2.9 (m, 3H), 3.3 (t, IH)5 3.5 (m, 3H), 3.7-3.9 (m, 2H).
With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 2h;
Benzyl bromide (1.2 g, 7.06 mmol) was added in one portion to a stirred solution of (R)- morpholin-3-ylmethanol (986 mg, 6.42 mmol) and DIPEA (1.66 g, 12.8 mmol) in MeCN (50 ml) and the resulting solution was stirred at rt for 2h, whereafter the mixture was then concentrated under reduced pressure. The afforded residue was dissolved in DCM (50ml) was and washed sequentially with sat. aq. NaHC03 (50 ml) and 1 M KOH (10 ml). The aqueous phase was extracted with DCM (25 ml) and the combined organic layers were dried over Na2S04, filtered and concentrated which gave the title compound (1.19 g, 89%). MS (ESI): 208 [M+H]+.
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