Diphosgene → 4-(4-Methoxy-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid 4-(5-methyl-pyridin-2-ylmethyl)-phenyl ester

HRID 1180076Notes

Reaction equation

HRID 1180076 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.C(N(C(C)C)C(C)C)C.Cl[C:26](OC(Cl)(Cl)Cl)=[O:27].[CH3:33][O:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]2[CH2:42][CH2:43][NH:44][CH2:45][CH:46]=2)=[CH:37][CH:36]=1>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][C:26]([N:44]3[CH2:43][CH:42]=[C:41]([C:38]4[CH:37]=[CH:36][C:35]([O:34][CH3:33])=[CH:40][CH:39]=4)[CH2:46][CH2:45]3)=[O:27])=[CH:13][CH:14]=2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 10426DiphosgeneHCID 81531DiisopropylethylamineHCID 135448404-(4-Methoxyphenyl)-1,2,3,6-tetrahydropyridineHCID 220478484-(5-Methyl-pyridin-2-ylmethyl)phenol

Product 1

HCID 695184164-(4-Methoxy-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid 4-(5-methyl-pyridin-2-ylmethyl)-phenyl esterYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of 4-(5-methyl-pyridin-2-ylmethyl)phenol (0.8 mmol) prepared as described above and ethyldiisopropylamine (1.5 mmol) in CH2Cl2 (5 mL) at −30° C. was added trichloromethyl chloroformate (1.0 mmol). The solution was stirred at −30° C. for 10 min and at reflux temperature for 2 h. The solution was evaporated to dryness and redissolved in CH2Cl2 (5 mL) and cooled to 0° C. before addition of 4-(4-methoxyphenyl)-1,2,3,6-tetrahydro-pyridine (1.5 mmol). The solution was stirred at room temperature for 16 h evaporated to give the crude product which was purified by FC (Quad flash 40 CH2Cl2:Et2O:Heptane:Et3N 1:1:2:0.25->1:1:1:0.25) to give the title compound in 10% yield as colorless crystals.

Workup

  1. customat −30° C.
  2. temperatureat reflux temperature for 2 h
  3. customThe solution was evaporated to dryness
  4. dissolutionredissolved in CH2Cl2 (5 mL)
  5. stirringThe solution was stirred at room temperature for 16 h
  6. customevaporated
  7. customto give the crude product which
  8. customwas purified by FC (Quad flash 40 CH2Cl2:Et2O:Heptane:Et3N 1:1:2:0.25->1:1:1:0.25)

Sources & evidence

ORD record
ord-4fdfab501b7d414981edee67ec3f4ff3
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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