反应详情

Add sodium borohydride (1.29 g, 34.1 mmol) to a stirred solution of 1-(benzyl-methyl-amino)-heptan-3-one (2.41 g, 10 mmol) and methanol (45 ml) at 0° C. under N2. Stir the reaction for 1 hr at 0° C. Quench the reaction with water at 0° C. and concentrate under reduced pressure. Dissolve the residue in ethyl acetate, wash with brine and dry over sodium sulfate. Filter off and concentrate to give the crude compound. Purify the compound by flash chromatography, eluting with 5% ethanol/0.5% ammonium hydroxide/chloroform to yield 2.22 g (91%) of 1-(benzyl-methyl-amino)-heptan-3-ol: mass spectrum (ion spray) m/z=236 (M+1); 1H NMR (CDCl3) δ 7.34-7.23 (m, 5H), 3.76-3.72 (m, 1H), 3.53 (dd, 2H), 2.80-2.73 (m, 1H), 2.59-2.53 (m, 1H), 2.21 (s, 1H), 1.68-1.62 (m, 1H), 1.57-1.29 (m, 7H), 0.91 (t, 3H).

1. customthe reaction for 1 hr at 0° C
2. customQuench
3. customthe reaction with water at 0° C.
4. concentrationconcentrate under reduced pressure
5. dissolutionDissolve the residue in ethyl acetate
6. washwash with brine
7. dry with materialdry over sodium sulfate
8. filtrationFilter off
9. concentrationconcentrate
10. customto give the crude compound
11. customPurify the compound by flash chromatography
12. washeluting with 5% ethanol/0.5% ammonium hydroxide/chloroform