Chloroform → Dimethyl 4,4a,9,9a-tetrahydro-1,3-dimethyl-3,9-methano-3H-indeno[2,1-c]pyridine-9a,10-dicarboxylate

HRID 279866Notes

Reaction equation

HRID 279866 reaction equation
[CH3:1][C:2]1[NH:3][CH2:4][C:5](C)([C:24]([O:26][CH3:27])=[O:25])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH:18]=[CH:19][Si](C)(C)C)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].[CH:29](Cl)(Cl)Cl>[Ti](Cl)(Cl)(Cl)Cl>[CH3:29][C:4]1[C:5]2([C:24]([O:26][CH3:27])=[O:25])[CH:6]3[CH:7]([C:8]([O:10][CH3:11])=[O:9])[C:2]([CH3:1])([CH2:19][CH:18]2[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]3=2)[N:3]=1

Participants

4

Reactant 2

HCID 6212ChloroformHCID 74031287Dimethyl 2,5-dimethyl-4-[2-(2-trimethylsilylethenyl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate

Product 1

HCID 13449182Dimethyl 4,4a,9,9a-tetrahydro-1,3-dimethyl-3,9-methano-3H-indeno[2,1-c]pyridine-9a,10-dicarboxylate

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Procedure

To the Compound 1b (1.0 mmol) in Chloroform (10 ml) was added titanium tetrachloride (1.1 mmol) under nitrogen at ambient temperature. After 3 hours, the solvent was removed in vacuo and the residue flash chromatographed on silica gel eluted with hexane:diethyl ether (1:2) to afford the desired product. The β-isomer was a white solid (Rf =0.4, m.p. 104.5°-105.5° C.). The α-isomer was a white solid (Rf =0.3, m.p. 160°-161.5° C.).

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue flash chromatographed on silica gel
  3. washeluted with hexane:diethyl ether (1:2)

Sources & evidence

ORD record
ord-a0baa3cde69e47279c6f829bb75cc706
Source dataset
uspto-grants-1986_05
Patent number
US04587253

Reaction notes

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