3-Acetylpyridine → HCID 86751250, compound

HRID 1378499Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[CH:10]([N-:13][CH:14]([CH3:16])C)([CH3:12])C.[Li+].[N-]1C=CN=[CH:19]1.[C:23]([O-:26])(O)=O.[Na+]>C1COCC1.CCCCCCC.C1COCC1.C(C1C=CC=CC=1)C>[OH:3][C:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)=[CH:2][C:23]([N:13]1[CH2:10][CH2:12][CH2:19][CH2:16][CH2:14]1)=[O:26]

Participants

Conditions

Temperature: -78 °C

Procedure

To a separate flask was added 3-acetylpyridine (0.27 g, 0.0021 mol) in THF (10 ml) and the solution cooled under N2 to -78° C. To this solution was added dropwise via syringe at -78° C. lithium diisopropylamide (1.1 ml of a 2M solution in heptane-THF-ethylbenzene, 0.0022 mol). After aging for 5 min., the imidazolide solution was added dropwise at -78° C. The resulting thick suspension was then allowed to stir to room temperature. After 2 h, the clear yellow solution was poured into saturated NaHCO3 solution and the aqueous layer was extracted with EtOAc (3×). The organic extracts were dried, filtered and concentrated to dryness. The crude residue was chromatographed on a Still column (40 mm) and the product eluted with 10% IPA/CHCl3 saturated with NH3 to yield 1-(tetralin-2-yl)-4-(1-(3-hydroxy-1-oxo-3-(3-pyridinyl)-2-propenyl)piperdine.

Workup

waitAfter 2 h
extractionthe aqueous layer was extracted with EtOAc (3×)
customThe organic extracts were dried
filtrationfiltered
concentrationconcentrated to dryness
customThe crude residue was chromatographed on a Still column (40 mm)
washthe product eluted with 10% IPA/CHCl3 saturated with NH3

Sources & evidence

ORD record: ord-8d258b57ec97464e991f1ba43cfe29f2
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05668148

Reaction notes

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