Triphenylphosphine → 2-((R)-1-chloro-ethyl)-isonicotinonitrile

反応式

O[C@H:2]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][N:11]=1)[C:7]#[N:8])[CH3:3].C1C(=O)N([Cl:19])C(=O)C1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>>[Cl:19][C@@H:2]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][N:11]=1)[C:7]#[N:8])[CH3:3]

参加物

反応物 3

HCID 11776Triphenylphosphine2 回

HCID 31398Chlorosuccinimide2 回

HCID 598688242-((S)-1-Hydroxy-ethyl)-isonicotinonitrile

生成物 1

HCID 598688402-((R)-1-chloro-ethyl)-isonicotinonitrile収率 7%

反応条件

温度: 30 °C

実験手順

The title compound was prepared from 2-((S)-1-hydroxy-ethyl)-isonicotinonitrile (620 mg, 4.18 mmol) according to General Method C, except that 1.0 equiv. NCS and 1.0 equiv. PPh3 were used. After 24 hrs reaction time another 0.2 equiv. each of NCS and PPh3 were added and the temperature was increased to 30° C. for 12 h. Workup and purification by flash column chromatography yielded the title compound (46 mg, 7% yield) with 82% ee. 1H NMR (CDCl3) δ 8.74 (d, 1H), 7.76 (s, 1H), 7.46 (dd, 1H), 5.16 (q, 1H), 1.88 (d, 3H).