Réaction #1702044

Équation de réaction

NaHSO3

NaI

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

chlorotrimethylsilane

→

title compound

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

Solvants

DCM

acetonitrile

Conditions de réaction

Traitement

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

Mode opératoire

(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