HRID72178

反应详情

EQUATION

反应方程式

HRID 72178 的结构方程式

AUXILIARIES

试剂、催化剂与溶剂

1

CONDITIONS

反应条件

温度
0 °C

PROCEDURE

实验过程

(S)—N-(1-hydroxybutan-2-yl)-4-methylbenzene-sulfonamide (800 mg, 3 mmol) was dissolved in dichloromethane (20 mL) and triethylamine (0.92 mL, 6.6 mmol) was added. The mixture was stirred at 0° C. for 10 minutes. Diphenyl(vinyl)sulfonium trifluoromethanesulfonate (1.25 g, 3.45 mmol), dissolved in dichloromethane (10 mL) was added dropwise over 5 minutes. The mixture was stirred while allowed to warm up to room temperature overnight. Saturated aqueous NH4Cl was added and the phases were separated. The aqueous phase was extracted with 2×30 mL of DCM. The combined organic phases were dried with MgSO4 and filtered. The filtrate was concentrated on silica gel and purified by flash chromatography (100% Hex to 60% EtOAc/Hex) to give (S)-3-ethyl-4-tosylmorpholine (j-3) as a white solid: 1H NMR (400 MHz, CDCl3) δ 7.71 (d, J=8.3 Hz, 2H), 7.30 (t, J=8.3 Hz, 2H), 3.77-3.60 (m, 3H), 3.60-3.44 (m, 2H), 3.44-3.19 (m, 3H), 2.43 (s, 3H), 1.67 (dtd, J=28.6, 14.0, 7.4 Hz, 2H), 1.31-1.12 (m, 2H), 0.97-0.84 (m, 3H); LC-MS: m/z=270 (M+H).

WORKUP

后处理

  1. additionwas added dropwise over 5 minutes
  2. stirringThe mixture was stirred while
  3. temperatureto warm up to room temperature overnight
  4. customthe phases were separated
  5. extractionThe aqueous phase was extracted with 2×30 mL of DCM
  6. dry with materialThe combined organic phases were dried with MgSO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated on silica gel
  9. custompurified by flash chromatography (100% Hex to 60% EtOAc/Hex)