2,3-Dichlorobenzaldehyde → 5-Cyclopentyl 3-methyl 4-(2,3-dichlorophenyl)-2-(fluoromethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate

HRID 1789010Notes

Reaction equation

HRID 1789010 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[F:11][CH2:12][C:13](=O)[CH2:14][C:15]([O:17][CH3:18])=[O:16].[NH2:20][C:21]([CH3:31])=[CH:22][C:23]([O:25][CH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:24]>C(OCC)(=O)C>[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[C:22]([C:23]([O:25][CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)=[O:24])=[C:21]([CH3:31])[NH:20][C:13]([CH2:12][F:11])=[C:14]1[C:15]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 3

HCID 357452,3-DichlorobenzaldehydeHCID 14170515Methyl 4-fluoro-3-oxobutanoateHCID 66992092Cyclopentyl 3-aminobut-2-enoate

Product 1

HCID 700905275-Cyclopentyl 3-methyl 4-(2,3-dichlorophenyl)-2-(fluoromethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylateYield 28.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2,3-Dichlorobenzaldehyde (1.31 g, 7.5 mmoles), methyl 4-fluoro-3-oxobutanoate (1.0 g, 7.5 mmoles) and cyclopentyl 3-amino-2-butenoate (1.26 g, 7.5 mmoles) were heated at 90° with stirring under nitrogen for 2.5 hours. The reaction mixture was dissolved in ethyl acetate, dried (MgSO4) and the solvent was removed in vacuo. The residue was chromatographed on silica eluting with ethyl acetate/methylene chloride mixtures. The title compound (0.95 g) was obtained after crystallisation from petroleum ether (60°-80) mp 148°-50°.

Workup

  1. dry with materialdried (MgSO4)
  2. customthe solvent was removed in vacuo
  3. customThe residue was chromatographed on silica eluting with ethyl acetate/methylene chloride mixtures

Sources & evidence

ORD record
ord-5099b83648494d408f4009e510dc0900
Source dataset
uspto-grants-1987_08
Patent number
US04686217

Reaction notes

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