反应详情

1-Benzyl-3-piperidone hydrochloride monohydrate (5.93 g, 26.3 mmol) was partitioned between a saturated aqueous NaHCO3 solution (30 ml) and CH2Cl2 (50 mL). The organic layer was separated and dried over Na2SO4 and filtered. The filtrated was collected and (1R,2R)-cyclohexane-1,2-diamine (3 g, 26.3 mmol) was added followed by sodium triacetoxy borohydride (8.35 g, 39.4 mmol). The reaction was stirred at rt overnight. After this time, the reaction was quenched with water (2 ml). The resulting solution was washed with saturated aqueous NaHCO3 (50 ml) and saturated NaCl (50 ml). The organic layer was dried over MgSO4, filtered and concentrated. The resulting residue was purified by RP Prep-HPLC. The desired fractions containing the product were concentrated to give the product, (1R,2R)—N1-(1-benzylpiperidin-3-yl)cyclohexane-1,2-diamine (3.01 g, 10.47 mmol, 40% yield) as a trifluoroacetate salt and as a white solid. 1H NMR (500 MHz, MeOH-d3) δ ppm 7.54-7.36 (m, 5H), 4.27-3.99 (m, 2H), 3.24-2.94 (m, 3H), 2.69 (d, J=9.90 Hz, 2H), 2.46-2.27 (m, 1H); 2.25-2.02 (m, 2H); 2.03-1.83 (m, 2H); 1.83-1.62 (m, 4H); 1.47-1.19 (m, 4H); 1.05 (d, J=11.55 Hz, 1H). 13C NMR (126 MHz, MeOH-d3) δ ppm 132.27, 130.75, 130.25, 62.31, 58.81, 56.46, 53.57, 32.76, 31.33, 25.99, 25.73, 25.40

1. customThe organic layer was separated
2. dry with materialdried over Na2SO4
3. filtrationfiltered
4. customThe filtrated was collected
5. customAfter this time, the reaction was quenched with water (2 ml)
6. washThe resulting solution was washed with saturated aqueous NaHCO3 (50 ml) and saturated NaCl (50 ml)
7. dry with materialThe organic layer was dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated
10. customThe resulting residue was purified by RP Prep-HPLC
11. additionThe desired fractions containing the product
12. concentrationwere concentrated