تفاعل #78272

معادلة التفاعل

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

ظروف التفاعل

المعالجة

1. 1
   أخرىquenched with concentrated aqueous NH4OH
2. 2
   workup.ADDITIONdiluted with methylene chloride and water
3. 3
   أخرىThe aqueous layer is separated
4. 4
   استخلاصextracted with methylene chloride
5. 5
   غسيلwashed with saturated NaCl
6. 6
   تجفيفdried over Na2SO4
7. 7
   تركيزconcentrated in vacuo
8. 8
   أخرىThe resultant residue is purified by flash chromatography (silica gel, EtOAc/MeOH/NH4OH: 9/1/0.05)

الإجراء التجريبي

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%).

المصدر