Triethylamine → Methyl 1-benzyloxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylate

HRID 1003381Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]=[C:3]([C:7]([O:9][CH3:10])=[O:8])[CH2:2]1.C(N(CC)CC)C.Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>C(Cl)Cl>[CH2:22]([O:21][C:19]([N:1]1[CH2:6][CH2:5][CH:4]=[C:3]([C:7]([O:9][CH3:10])=[O:8])[CH2:2]1)=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: -15 °C

Procedure

Arecoline (39.5 g, 0.25 mol) was dissolved in dry toluene (20 ml). 1-Chloroethyl chloroformate (30.5 ml) was added slowly at 0-5° C. The mixture was heated at 80° C. for 2 h, cooled to room temperature, filtered and evaporated to dryness in vacuo. The residue was dissolved in methylene chloride (400 ml) and extracted with 10% aqueous sodium carbonate. The organic layer was dried over magnesium sulfate, filtered and evaporated to dryness to give methyl 1,2,5,6-tetrahydropyridine-3-carboxylate (Yield: 30.5 g, 85%). Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate (1.1 g, 7.8 mmol) was dissolved in methylene chloride (20 ml) and cooled to -15° C. Triethyl amine (2.2 ml, 15,8 mmol) and a solution of benzyl chloroformate (1.2 ml, 8,4 mmol) in methylene chloride (10 ml) were added. Stirring at room temperature for 1.5 h followed by evaporation to dryness. The residue was dissolved in methylene chloride and extracted with water two times. The organic layer separated, dried and evaporated to dryness in vacuo to give methyl 1-benzyloxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylate as an oil (Yield: 2.0 g, 92%).

Workup

customfollowed by evaporation to dryness
dissolutionThe residue was dissolved in methylene chloride
extractionextracted with water two times
customThe organic layer separated
customdried
customevaporated to dryness in vacuo

Sources & evidence

ORD record: ord-e6c5a213837f49e0a9ee6917641ff2e9
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06046214

Reaction notes

Loading…