Reaction #57336

Reaction equation

4

1-(1-Naphthalen-1-yl-ethyl)-6-phenethyl-octahydro-pyrrolo[2,3-c]pyridin-7-one

DIBAL

toluene

→

title compound

Yield 49.8%

1-(1-Naphthalen-1-yl-ethyl)-6-phenethyl-octahydro-pyrrolo[2,3-c]pyridine

Yield 49.8%

Solvents

THF

Conditions

Workup

1. 1
   Otherquenched with 20 mL of water
2. 2
   OtherThe solvent is evaporated
3. 3
   workup.ADDITIONthe residue is diluted with 100 mL of 1:1 saturated Rochells salt/15% NaOH
4. 4
   Extractionthis extracted with EtOAc (4×50 mL)
5. 5
   Otherdried
6. 6
   Concentrationconcentrated under vacuum
7. 7
   OtherThe residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:9)

Procedure

To a solution of 4 (4.8 g, 12 mmol) in THF (100 mL) is added slowly 1 M DIBAL in toluene, (50 mL, 50 mmol) at −78° C. The mixture is stirred at room temperature for 1 hour and quenched with 20 mL of water. The solvent is evaporated, the residue is diluted with 100 mL of 1:1 saturated Rochells salt/15% NaOH, and this extracted with EtOAc (4×50 mL). The organic extracts are combined, dried and concentrated under vacuum. The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:9) to provide 2.3 g (48%) of the title compound. M+H+=385.26.

Source