反应 #1702044

ord-cdd11e4a755c4198a40ef2c5174e1e4f

反应方程式

O=S([O-])O.[Na+]
NaHSO3
[I-].[Na+]
NaI
COc1ccc([C@H]2CCC(=O)C2)cn1
(3S)-3-(6-methoxy-3-pyridyl)cyclopentanone
C[Si](C)(C)Cl
chlorotrimethylsilane
O=C1CC[C@H](c2ccc(=O)[nH]c2)C1
title compound
O=C1CC[C@H](c2ccc(=O)[nH]c2)C1
5-[(1S)-3-Oxocyclopentyl]-1H-pyridin-2-one

反应条件

温度
100°CELSIUS
详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    洗涤the mixture was washed with water
  2. 2
    干燥The organic phase was dried over MgSO4
  3. 3
    浓缩concentrated under reduced pressure

实验过程

(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).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08765676B2uspto-grants-2014_07