Sodium Methoxide → HCID 12621371, compound

HRID 1730162Notes

Reaction equation

HRID 1730162 reaction equation
Cl[N:2]1[C@@H:6]([C:7]2[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[C:9]([O:17][CH3:18])[CH:8]=2)[CH2:5][C@H:4]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[C:3]1([CH3:26])[CH3:25].C[O-].[Na+]>O>[CH3:25][C:3]1([CH3:26])[N:2]=[C:6]([C:7]2[CH:8]=[C:9]([O:17][CH3:18])[C:10]([O:15][CH3:16])=[C:11]([O:13][CH3:14])[CH:12]=2)[CH2:5][CH:4]1[C:19]1[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86734172HCID 86734172, compound

Product 1

HCID 12621371HCID 12621371, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9.8 G. of 4-[trans-1-chloro-2,2-dimethyl-5-(3,4,5-trimethoxyphenyl)-3-pyrrolidinyl]-pyridine are treated with 52 ml. of sodium methylate solution (10 g. of sodium per 100 ml. of methanol) and heated at 50° C. for 3 hours. Then the reaction mixture is treated with water and extracted three times with ethyl acetate. The organic phase is washed with water, dried over sodium sulfate and evaporated under reduced pressure. The residue is crystallized with ethyl acetate/isopropyl ether to yield 4-(5,5-dimethyl-2-(3,4,5-trimethoxyphenyl)-1-pyrrolin-4-yl)-pyridine, melting point 143°-144° C. This compound is, as in Example 37, reduced with sodium borohydride to the cis-pyrrolidinyl compound. This example shows therefore the isomerization of trans/pyrrolidines by way of a pyrroline to the corresponding cis-pyrrolidine.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue is crystallized with ethyl acetate/isopropyl ether

Sources & evidence

ORD record
ord-5a3f232d459548d6a2a5bf6c27713b12
Source dataset
uspto-grants-1976_11
Patent number
US03991197

Reaction notes

Loading…