Реакция #2446079

Уравнение реакции

Sodium borohydride

1-amino-2-propanol

cyclohexanone

→

1-(cyclohexylamino)propan-2-ol

Растворители

ethanol

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirred at rt for 15 minutes
2. 2
   ДругоеThe resultant reaction mixture
3. 3
   Другоеwas quenched with water
4. 4
   Фильтрацияfiltered through the Celite® reagent, and solvent
5. 5
   Другоеwas evaporated
6. 6
   workup.DISSOLUTIONThe residue was dissolved in 2N HCl
7. 7
   Промывкаwashed with ethyl acetate
8. 8
   ЭкстракцияThe compound was extracted with ethyl acetate
9. 9
   СушкаThe organic layer was dried over sodium sulphate
10. 10
    Концентрированиеconcentrated to dryness

Методика

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).

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