2-Acetylpyridine-4-carbonitrile → 2-((S)-1-Hydroxy-ethyl)-isonicotinonitrile

HRID 1694555Notes

Reaction equation

HRID 1694555 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][N:11]=1)[C:7]#[N:8])(=[O:3])[CH3:2].B(Cl)([C@H]1[C@@H](C)[C@H]2C(C)(C)[C@H](C2)C1)[C@H]1[C@@H](C)[C@H]2C(C)(C)[C@H](C2)C1>>[OH:3][C@H:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][N:11]=1)[C:7]#[N:8])[CH3:2]

Participants

3

Reactant 2

HCID 104644602-Acetylpyridine-4-carbonitrileHCID 86625794(-)-DIPCl

Product 1

HCID 598688242-((S)-1-Hydroxy-ethyl)-isonicotinonitrileYield 30.8%

Procedure

The title compound was prepared according to General Method B starting from 2-acetyl-isonicotinonitrile (2.00 g, 13.7 mmol) and (−)-DIPCl (6.58 g, 20.53 mmol) to yield the title compound (625 mg, 4.22 mmol) with 90% ee.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-d958621412874553b29570b5eeb0e624
Source dataset
uspto-grants-2012_04
Patent number
US08158785B2

Reaction notes

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