Tributyrin → (S)-1-(3-Pyridyl)ethanol

HRID 1089086

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([OH:9])[CH3:8])[CH:2]=1.O=C(CCC)OCC(OC(=O)CCC)COC(=O)CCC>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C@@H:7]([OH:9])[CH3:8])[CH:2]=1

Participants

Reactant 2

HCID 6050Tributyrin

HCID 101192alpha-Methyl-3-pyridinemethanol

Product 1

HCID 10725338(S)-1-(3-Pyridyl)ethanolYield 33.7%

Procedure

1-(3-Pyridyl)ethanol (8.9 g), tributyrin (24.0 g) and an enzyme (Lipase CES made by Amano Seiyaku K. K.) (3.6 g) were agitated at 37° C. for 190 hours, followed by filtering off the enzyme and subjecting the filtrate to silica gel column chromatography using toluene as solvent to obtain (S)-1-(3-pyridyl)ethanol (3.0 g). According to a high-speed liquid chromatography using an optical resolution column (CHIRAL CEL OB, trademark of product made by Daicel Co., Ltd.), its optical purity was 80% ee or higher.

Workup

filtrationby filtering off the enzyme

Sources & evidence

ORD record: ord-0b6b26a7d5e64ab49f373c601675e552
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04965018

Linked notes

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