3-Acetylpyridine → (1R)-1-(pyridin-4-yl)ethan-1-ol

HRID 1089089Notes

Reaction equation

C(C1C=NC=CC=1)(=O)C.[C:10]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)(=[O:12])[CH3:11]>>[N:16]1[CH:17]=[CH:18][C:13]([C@H:10]([OH:12])[CH3:11])=[CH:14][CH:15]=1

Participants

Reactant 2

HCID 95893-Acetylpyridine

HCID 142824-Acetylpyridine

Product 1

HCID 11804747(1R)-1-(pyridin-4-yl)ethan-1-ol

Procedure

Example 1 was repeated except that 3-acetylpyridine used in Example 1 was replaced by 4-acetylpyridine to obtain (R)-1-(4-pyridyl)ethanol. [a]D25 =+32.4° (c=1.0, EtOH). Its optical purity was 99% ee or higher according to a high-speed liquid chromatography using an optical resolution column (CHIRAL CEL OB made by Daicel K. K.).

Sources & evidence

ORD record: ord-2ae304ba4ce94eb5a19432e9cf616993
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04965018

Reaction notes

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