反应详情

The crude mixture containing N-[4-[3-(ethylheptylamino)-1-oxopropyl]phenyl]methanesulfonamide hydrochloride from Preparation 16 (1.0 g, 2.6 mmol) is transferred to a reaction flask in ethanol-carbon tetrachloride, concentrated, treated with benzene and concentrated again in vacuo. The residue in 18 ml of ethanol, under nitrogen, is cooled in an ice bath and treated with powdered NaBH4 (0.23 g, 0.006 mol) in portions (foaming) over 20 min. The mixture is stirred for 15 min in the cold and for 2.5 hrs at room temperature. It is then treated with 20 ml of ice-water in portions over 5 min. Chloroform (10 ml) is added to the resultant suspension; the mixture is stirred 5 min; and, the layers are separated. The aqueous phase is extracted with additional chloroform (3×50 ml). (Each extract is backwashed with 5 ml of H2O). The pooled organic extract is washed with brine, dried (Na2SO4) and concentrated to give 0.85 g of crude material (two main spots by TLC). This material is chromatographed over 250 ml of silica gel with 0.5% NH4OH/7.5% MeOH/CHCl3 ; 16 ml fractions are collected. Fractions at approximately 36-54 give the title compound which is crystallized from ether-pentane; m.p. 74°-75° C.

1. concentrationconcentrated
2. additiontreated with benzene
3. concentrationconcentrated again in vacuo
4. temperatureThe residue in 18 ml of ethanol, under nitrogen, is cooled in an ice bath
5. stirringthe mixture is stirred 5 min
6. customand, the layers are separated
7. extractionThe aqueous phase is extracted with additional chloroform (3×50 ml)
8. extractionThe pooled organic extract
9. washis washed with brine
10. dry with materialdried (Na2SO4)
11. concentrationconcentrated
12. customto give 0.85 g of crude material (two main spots by TLC)
13. customThis material is chromatographed over 250 ml of silica gel with 0.5% NH4OH/7.5% MeOH/CHCl3
14. custom16 ml fractions are collected