Reaction #2069974

Reaction equation

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

Conditions

Workup

1. 1
   Otherquenched with concentrated aqueous NH4OH
2. 2
   workup.ADDITIONdiluted with methylene chloride and water
3. 3
   OtherThe aqueous layer is separated
4. 4
   Extractionextracted with methylene chloride
5. 5
   Washwashed with saturated NaCl
6. 6
   Dryingdried over Na2SO4
7. 7
   Concentrationconcentrated in vacuo
8. 8
   OtherThe resultant residue is purified by flash chromatography (silica gel, EtOAc/MeOH/NH4OH: 9/1/0.05)

Procedure

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%).

Source