반응 #81928

반응 방정식

propionaldehyde

6-[4-(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)-1-butynyl]-3-pyridinamine

acetic acid

sodium triacetoxyborohydride

→

title compound

6-[4-(3,6-Dihydro-4-phenyl-1(2H)-pyridinyl)-1-butynyl]-N-propyl-3-pyridinamine

용매

dichloroethane

반응 조건

후처리

1. 1
   기타The reaction is quenched with saturated aqueous sodium bicarbonate
2. 2
   workup.ADDITIONdiluted with dichloromethane
3. 3
   건조the organic layer is dried (sodium sulfate)
4. 4
   농축concentrated under reduced pressure
5. 5
   기타The residue is chromatographed (silica gel, 1% methanol/99% dichloromethane)

실험 절차

A solution of propionaldehyde (0.18 mL, 2.5 mmol), 6-[4-(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)-1-butynyl]-3-pyridinamine (Example 20) (0.83 g, 2.7 mmoL) and glacial acetic acid (0.14 mL, 2.5 mmol) in 20 mL of dichloroethane is treated with sodium triacetoxyborohydride (0.79 g, 3.7 mmol) under nitrogen and is stirred at room temperature for 18 hours. The reaction is quenched with saturated aqueous sodium bicarbonate, diluted with dichloromethane, and the organic layer is dried (sodium sulfate) and concentrated under reduced pressure. The residue is chromatographed (silica gel, 1% methanol/99% dichloromethane) to give the title compound, containing 0.20 mol of water; mp 138°-139° C.

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