반응 #78272

반응 방정식

acetic acid

2-{[1-(phenylsulfonyl)-1H-indole-4-yl]oxy}ethylamine

tetrahydro-4H-pyran-4-one

sodium triacetoxyborohydride

1,2-dichloroethane

→

title product

N-(2-{[1-(Phenylsulfonyl)-1H-indol-4-yl]oxy}ethyl)tetrahydro-2H-pyran-4-amine hydrochloride

반응 조건

후처리

1. 1
   기타quenched with concentrated aqueous NH4OH
2. 2
   workup.ADDITIONdiluted with methylene chloride and water
3. 3
   기타The aqueous layer is separated
4. 4
   추출extracted with methylene chloride
5. 5
   세척washed with saturated NaCl
6. 6
   건조dried over Na2SO4
7. 7
   농축concentrated in vacuo
8. 8
   기타The resultant residue is purified by flash chromatography (silica gel, EtOAc/MeOH/NH4OH: 9/1/0.05)

실험 절차

A mixture of 2-{[1-(phenylsulfonyl)-1H-indole-4-yl]oxy}ethylamine (0.316 g, 1.0 mmol), tetrahydro-4H-pyran-4-one (0.09 ml, 1.00 mmol) and sodium triacetoxyborohydride (0.312 g, 1.4 mmol) in 1,2-dichloroethane is treated with acetic acid (0.06 ml) at room temperature, stirred under nitrogen for 18 hr, quenched with concentrated aqueous NH4OH and diluted with methylene chloride and water. The aqueous layer is separated and extracted with methylene chloride. The organic layer and extracts are combined, washed with saturated NaCl, dried over Na2SO4, and concentrated in vacuo. The resultant residue is purified by flash chromatography (silica gel, EtOAc/MeOH/NH4OH: 9/1/0.05) to afford the free amine of the title product as a clear oil, 0.36 g (90%).

출처