Reaction #1702044

Reaction equation

NaHSO3

NaI

(3S)-3-(6-methoxy-3-pyridyl)cyclopentanone

chlorotrimethylsilane

→

title compound

5-[(1S)-3-Oxocyclopentyl]-1H-pyridin-2-one

Solvents

DCM

acetonitrile

Conditions

Workup

1. 1
   Washthe mixture was washed with water
2. 2
   DryingThe organic phase was dried over MgSO4
3. 3
   Concentrationconcentrated under reduced pressure

Procedure

(3S)-3-(6-methoxy-3-pyridyl)cyclopentanone (preparation 3) (560 mg, 2.9 mmol) was dissolved in acetonitrile (12 mL) and treated with NaI (1.32 g, 8.8 mmol) followed by chlorotrimethylsilane (0.74 mL, 5.9 mmol). The reaction mixture was heated in a microwave reactor at 100° C. for 5 min. Following the addition of DCM and aqueous NaHSO3, the mixture was washed with water. The organic phase was dried over MgSO4 and concentrated under reduced pressure to afford the title compound. 1H NMR (300 MHz, DMSO) δ 11.43 (s, 1H), 7.50 (dd, 1H), 7.19 (d, 1H), 6.32 (d, 1H), 3.21-3.06 (m, 1H), 2.46-2.35 (m, 1H), 2.33-2.11 (m, 4H), 1.90-1.69 (m, 1H).

Source