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

HRID 2422186Notes

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

Reactant 2

HCID 104644602-Acetylpyridine-4-carbonitrile

HCID 86625794(-)-DIPCl

Product 1

HCID 598688242-((S)-1-Hydroxy-ethyl)-isonicotinonitrileYield 78.5%

Procedure

The title compound (1.13 g, 7.63 mmol) was prepared according to General Method E1 starting from 2-acetyl-isonicotinonitrile (1.42 g, 9.72 mmol) and (−)-DIPCl (4.67 g, 14.57 mmol).

Sources & evidence

ORD record: ord-915dc229d7704dcbb5ce6a0b569369df
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960395B2

Reaction notes

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