반응 #2446079

반응 방정식

Sodium borohydride

1-amino-2-propanol

cyclohexanone

→

1-(cyclohexylamino)propan-2-ol

용매

ethanol

반응 조건

후처리

1. 1
   workup.STIRRINGstirred at rt for 15 minutes
2. 2
   기타The resultant reaction mixture
3. 3
   기타was quenched with water
4. 4
   여과filtered through the Celite® reagent, and solvent
5. 5
   기타was evaporated
6. 6
   workup.DISSOLUTIONThe residue was dissolved in 2N HCl
7. 7
   세척washed with ethyl acetate
8. 8
   추출The compound was extracted with ethyl acetate
9. 9
   건조The organic layer was dried over sodium sulphate
10. 10
    농축concentrated to dryness

실험 절차

To a solution of 1-amino-2-propanol (15 g, 0.199 mol) in ethanol (300 ml) was added cyclohexanone (31.4 mL, 0.299 mol). The reaction mixture was stirred at 0-10° C. for 10 minutes. Sodium borohydride (10.8 g, 0.285 mol) was added at 0° C., then stirred at rt for 15 minutes. The resultant reaction mixture was quenched with water, filtered through the Celite® reagent, and solvent was evaporated. The residue was dissolved in 2N HCl, washed with ethyl acetate; the pH of the aqueous layer was adjusted to 8 using saturated sodium bicarbonate solution. The compound was extracted with ethyl acetate. The organic layer was dried over sodium sulphate, concentrated to dryness, and the crude material was subjected to column chromatography to obtain 1-(cyclohexylamino)propan-2-ol. Yield: 22 g (70.1%); 1H NMR (400 MHz, DMSO-d6) δ 8.25 (bs, 1 H), 5.25 (bs, 1 H), 3.95-3.91 (m, 1 H), 2.89-2.88 (dd, J=6, 9 Hz, 2 H), 2.71-2.66 (m, 1 H), 2.00-1.99 (m, 2 H), 1.75-1.72 (m, 2 H), 1.60-1.57 (m, 1 H), 1.36-0.93 (m, 8 H).

출처