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

HRID 2267696Notes

Reaction equation

HRID 2267696 reaction equation
[NH:1]1[CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].[CH:13]1[CH:18]=[CH:17][C:16]([CH2:19][O:20][C:21](Cl)=[O:22])=[CH:15][CH:14]=1>[Cl-].[Na+].O>[CH2:19]([O:20][C:21]([N:1]1[CH2:2][CH:3]=[CH:4][CH2:5][CH2:6]1)=[O:22])[C:16]1[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 127501,2,3,6-Tetrahydropyridine

Product 1

HCID 11458613Benzyl 5,6-dihydropyridine-1(2H)-carboxylate

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

1,2,3,6-Tetrahydro-pyridine (3 g, 36.1 mmol) are treated with 10% aqueous sodium carbonate (2.1 ml) and cooled to 0° C. Within 1 h, benzyl chloroformiate (Z-chloride, 5.1 ml, 36 mmol) is added dropwise within 1 h. After additional stirring for 2 h, the mixture is treated with 30 ml of brine and extracted four times with diethyl ether. The organic layers are dried over sodium sulphate and evaporated. The crude product, 7 g of a colorless oil, is purified by Flash-chromatography (silica gel, cyclohexane/ethyl acetate 9:1).

Workup

  1. extractionextracted four times with diethyl ether
  2. dry with materialThe organic layers are dried over sodium sulphate
  3. customevaporated
  4. customThe crude product, 7 g of a colorless oil, is purified by Flash-chromatography (silica gel, cyclohexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-1a56c1c05ea944fa8179b4c59835a9de
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

Loading…