反应 #554685

反应方程式

3-[1-(tert-Butoxycarbonylamino)ethyl]benzoic acid

borane dimethylsulfide

→

sub-title compound

收率 68.5%

tert-Butyl N-[1-[3-(hydroxymethyl)phenyl]ethyl]carbamate

收率 68.5%

溶剂

THF

THF

反应条件

后处理

1. 1
   其他quenched with MeOH
2. 2
   其他The solvents were removed under reduced pressure
3. 3
   其他the resulting residue partitioned between 1M HCl and ethyl acetate
4. 4
   洗涤The organic layer was washed with saturated sodium bicarbonate (×1) and brine (×1)
5. 5
   干燥dried (Na2SO4)
6. 6
   过滤filtered
7. 7
   浓缩concentrated in vacuo
8. 8
   其他The residue was purified by column chromatography (ISCO Companion™ eluting with 0 to 30% EtOAc/petroleum ether)

实验过程

3-[1-(tert-Butoxycarbonylamino)ethyl]benzoic acid (7.57 g, 28.53 mmol) was dissolved in anhydrous THF (45 mL) and 2M borane-dimethylsulfide in THF (42.8 mL, 85.6 mmol) was added dropwise at ambient temperature. The reaction was stirred at this temperature for 3 hours then cooled to 0° C. and quenched with MeOH. The solvents were removed under reduced pressure and the resulting residue partitioned between 1M HCl and ethyl acetate. The organic layer was washed with saturated sodium bicarbonate (×1) and brine (×1), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion™ eluting with 0 to 30% EtOAc/petroleum ether) to give the sub-title compound as a white solid (4.91 g, 68% Yield). 1H NMR (400 MHz, DMSO) δ 1.28 (d, 3H), 1.36 (s, 9H), 4.47 (d, 2H), 4.54-4.64 (m, 1H), 5.17 (t, 1H), 7.14 (d, 2H), 7.23 (d, 2H) and 7.38 (d, 1H) ppm; MS (ES+) 252.3.

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