反応 #1584198

反応方程式

Cis-N-benzhydryl-4-phenylcyclohexanamine

4-phenylcyclohexanone

diphenylmethanamine

sodium triacetoxyborohydride

→

trans-N-benzhydryl-4-phenylcyclohexanamine

収率 19.5%

溶媒

DCE

反応条件

後処理

1. 1
   その他A white suspension resulted
2. 2
   その他was removed
3. 3
   その他The reaction was quenched with water carefully
4. 4
   workup.ADDITIONsaturated NaHCO3 was added carefully
5. 5
   抽出the aqueous portion was extracted with DCM (3×)
6. 6
   洗浄washed with brine
7. 7
   乾燥dried over Na2SO4
8. 8
   ろ過filtered
9. 9
   濃縮concentrated
10. 10
    その他The residue was purified by flash chromatography (0-100% hexane/EtOAc)

実験手順

Cis-N-benzhydryl-4-phenylcyclohexanamine: To a solution of 4-phenylcyclohexanone (500 mg, 2.87 mmol) and diphenylmethanamine (526 mg, 2.87 mmol) in DCE (4 mL) at 0° C. was added sodium triacetoxyborohydride (912 mg, 4.30 mmol) by portions slowly. A white suspension resulted and was stirred for 5 min before the ice-water bath was removed. The reaction was stirred at rt for 1.5 h. The reaction was quenched with water carefully, then saturated NaHCO3 was added carefully and the aqueous portion was extracted with DCM (3×). The organic layers were combined, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (0-100% hexane/EtOAc) to give Intermediate 1A (734 mg, 2.15 mmol, 74.9% yield) and trans-N-benzhydryl-4-phenylcyclohexanamine (191 mg, 0.559 mmol, 19.5% yield), LC-MS (ESI) m/z 342.1 (M+H), RT=1.76 min (Method B). 1H NMR (400 MHz, chloroform-d) δ ppm 7.37 (4H, d, J=7.33 Hz), 7.23-7.31 (6H, m), 7.11-7.23 (5H, m), 4.91 (1H, s), 2.80-2.88 (1H, m), 2.46-2.56 (1H, m), 1.74-1.90 (4H, m), 1.60-1.70 (2H, m), 1.47-1.59 (2H, m).

出典