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

HRID 1499465Notes

Reaction equation

HRID 1499465 reaction equation
[NH:1]1[CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1.C(Cl)Cl.[CH2:10]([O:17][C:18](ON1C(=O)CCC1=O)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>CCOC(C)=O.O>[N:1]1([C:18]([O:17][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:19])[CH2:2][CH:3]=[CH:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 127501,2,3,6-TetrahydropyridineHCID 83172Benzyl succinimido carbonate

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

1,2,3,6-Tetrahydropyridine (4.90 g, 58.9 mmol), DCM (40 mL), N-(benzyloxycarbonyloxy)succinimide (15.2 g, 61.0 mmol) and triethylamine (10.0 mL, 71.7 mmol) were mixed together and stirred at room temperature for 16 h. The reaction mixture was diluted with EtOAc and water. The organic layer was dried, filtered and concentrated under reduced pressure. The resulting residue was purified by chromatography on silica gel eluting with EtOAc in hexanes (0 to 40%) to give the sub-title compound as clear oil. LCMS calc. for C13H16NO2 (M+H)+: m/z=218.1. Found: 218.0.

Workup

  1. customThe organic layer was dried
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by chromatography on silica gel eluting with EtOAc in hexanes (0 to 40%)

Sources & evidence

ORD record
ord-54cd103cff854bbf9481d254f2acbc30
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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