Reaction #2432

Reaction equation

compound

Methyl 3-(2-oxo-1-piperidinyl)benzoate

borane tetrahydrofuran

→

oil

Yield 90.0%

Methyl 3-(1-piperidinyl)benzoate

Yield 90.0%

Solvents

THF

Conditions

Workup

1. 1
   Temperatureunder reflux for 1 h
2. 2
   Temperaturecooled
3. 3
   Otherevaporated
4. 4
   Temperatureheated
5. 5
   Temperatureunder reflux for 3 h
6. 6
   Otherevaporated
7. 7
   Otherchromatographed (eluant 10% EtOAc in hexanes)

Procedure

The compound of Example 37 (640 mg, 2.75 mmol) was dissolved in dry THF (30 ml) and borane-tetrahydrofuran complex (5 ml, 1M solution in THF) was added. The mixture was stirred under nitrogen under reflux for 1 h, then cooled and evaporated. The residue was taken up in MeOH/acetic acid (6/1, v/v, 70 ml) and heated under reflux for 3 h, then evaporated and chromatographed (eluant 10% EtOAc in hexanes) to provide a colourless oil (540 mg, 90%).

Source