Toluene → Benzyl 5,6-dihydropyridine-1(2H)-carboxylate

HRID 373698Notes

Reaction equation

HRID 373698 reaction equation
[C:1]([OH:5])(C)(C)C.S(C1C=CC(C)=CC=1)([O-])(=O)=[O:7].[NH+:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:23]1([CH3:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[N:17]1([C:1]([O:5][CH2:29][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:7])[CH2:22][CH2:21][CH:20]=[CH:19][CH2:18]1

Participants

4

Reactant 3

HCID 1140Toluene2×HCID 6386tert-ButanolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 11458613Benzyl 5,6-dihydropyridine-1(2H)-carboxylateYield 7.5%

Conditions

Temperature
100 °C

Procedure

A solution of the acyl azide in toluene (150 ml) was added dropwise to a toluene solution (150 ml) of t-butanol (30 ml) and pyridinium tosylate (9 mg) at 100° C. After completion of the addition, the reaction mixture was maintained at 100° C. for 12 hours. The reaction mixture was concentrated in vacuo, and the residue was chromatographed on silica gel (eluant: 20% ethyl acetate/hexane), providing the title compound as a viscous yellow oil, (2.4 g, 6.9 mmol, 7.5% yield from benzyl 1,2,5,6-tetrahydropyridine-1-carboxylate).

Workup

  1. additionAfter completion of the addition
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was chromatographed on silica gel (eluant: 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4546783628b7433fbe1cffd124cd0ca9
Source dataset
uspto-grants-1992_11
Patent number
US05164402

Reaction notes

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