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

HRID 1694556Notes

Reaction equation

HRID 1694556 reaction equation
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]

Participants

4

Reactant 3

HCID 11776Triphenylphosphine2×HCID 31398Chlorosuccinimide2×HCID 598688242-((S)-1-Hydroxy-ethyl)-isonicotinonitrile

Product 1

HCID 598688402-((R)-1-chloro-ethyl)-isonicotinonitrileYield 7%

Conditions

Temperature
30 °C

Procedure

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).

Workup

  1. additionwere added
  2. customWorkup and purification by flash column chromatography

Sources & evidence

ORD record
ord-f4229fa516fb4b7c9afb5967157b7b19
Source dataset
uspto-grants-2012_04
Patent number
US08158785B2

Reaction notes

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