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

HRID 258388Notes

Reaction equation

HRID 258388 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]=[C:4]([C:8]([OH:10])=[O:9])[CH2:3]1.Cl[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].[CH2:22](N(CC)CC)C.C(OCC)(=O)C.CCCCCC>C(Cl)Cl>[CH2:15]([O:14][C:12]([N:2]1[CH2:7][CH2:6][CH:5]=[C:4]([C:8]([O:10][CH3:22])=[O:9])[CH2:3]1)=[O:13])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 11957555Guvacine HydrochlorideHCID 21226206Ethyl acetate hexane

Product 1

HCID 18797103Methyl 1-benzyloxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylateYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,2,5,6-tetrahydro-3-pyridinecarboxylic acid, hydrochloride salt (1.8 g, 10 mmol) in methylene chloride (60 ml) was cooled to 0° C. Benzyl chloroformate (2.74 ml, 19.2 mmol) was added, followed by addition of triethylamine (7.2 ml, 51.2 mmol), and stirring at room temperature for 12 hours. The reaction mixture was washed with brine and dried over magnesium sulfate. Evaporation in vacuo afforded a yellow oil. This was purified by chromatography on silica gel (eluant: 20%, then 30% ethyl acetate/hexane) to give the product as a slightly yellow oil (2.14 g, 7.7 mmol, 77% yield).

Workup

  1. washThe reaction mixture was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation in vacuo
  4. customafforded a yellow oil
  5. customThis was purified by chromatography on silica gel (eluant

Sources & evidence

ORD record
ord-21afcc786973419ab2c38eadf785daa3
Source dataset
uspto-grants-1993_11
Patent number
US05266569

Reaction notes

Loading…