Reaction #2431

Reaction equation

bromide

Methyl 3-(5-bromopentanoylamino)benzoate

NaH

→

oil

Yield 56.2%

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

Yield 56.2%

Solvents

DMF

Conditions

Workup

1. 1
   workup.ADDITIONKI (80 mg) added
2. 2
   Temperaturethe mixture heated at 70° C. for 4 h
3. 3
   OtherThe mixture was evaporated
4. 4
   Otherpartitioned between EtOAc and 1M HCl
5. 5
   WashThe organic portion was washed with 5% KHCO3 and brine
6. 6
   Filtrationfiltered (Whatman® 1 PS, phase separator)
7. 7
   Otherevaporated
8. 8
   OtherThe residue was chromatographed (eluant 2% MeOH in EtOAc)

Procedure

The bromide of Example 36 (1.50 g, 4.88 mmol) was taken up in dry DMF (40 ml) and treated with NaH (160 mg, 80% disp. in oil) at 0° C. The mixture was stirred at r.t. under nitrogen for 10 min, then KI (80 mg) added and the mixture heated at 70° C. for 4 h. The mixture was evaporated and partitioned between EtOAc and 1M HCl. The organic portion was washed with 5% KHCO3 and brine, filtered (Whatman® 1 PS, phase separator) and evaporated. The residue was chromatographed (eluant 2% MeOH in EtOAc) to provide a colourless oil (640 mg, 56%).

Source