(+)2-Ethylthiomethyl-3-carboethoxy-5-carbomethoxy-4-(3-chlorophenyl)-6-methyl-1,4-dihydropyridine → (+)-2,6-Dimethyl-4-(3-chlorophenyl)-3-carboethoxy-5-carbomethoxy-1,4-dihydropyridine

HRID 5650Notes

Reaction equation

HRID 5650 reaction equation
C(S[CH2:4][C:5]1[NH:6][C:7]([CH3:27])=[C:8]([C:23]([O:25][CH3:26])=[O:24])[CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])C>CO>[CH3:4][C:5]1[NH:6][C:7]([CH3:27])=[C:8]([C:23]([O:25][CH3:26])=[O:24])[CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

3

Reactant 1

HCID 19796502(+)2-Ethylthiomethyl-3-carboethoxy-5-carbomethoxy-4-(3-chlorophenyl)-6-methyl-1,4-dihydropyridine

Product 1

HCID 5109984(+)-2,6-Dimethyl-4-(3-chlorophenyl)-3-carboethoxy-5-carbomethoxy-1,4-dihydropyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under nitrogen atmosphere and stirring, a MeOH solution (15 ml) of g 0.85 of (+)2-ethylthiomethyl-3-carboethoxy-5-carbomethoxy-4-(3-chlorophenyl)-6-methyl-1,4-dihydropyridine, cooled at 30° C. is treated with NaH2PO4 (g 1.45) and with Na/Hg amalgam (2.64 g) (10% in Na). After 15 minutes the solution is filtered and evaporated to a small volume under vacuum. The residue is partitioned between water (ml 20) and AcOEt (3×30 ml), the organic phases are collected to give after the usual work-up 0.56 g of (+)-2,6-dimethyl-4-(3-chlorophenyl)-3-carboethoxy-5-carbomethoxy-1,4-dihydropyridine [α]D =+5.5°; c=4.1 CH2Cl2.

Workup

  1. filtrationAfter 15 minutes the solution is filtered
  2. customevaporated to a small volume under vacuum
  3. customThe residue is partitioned between water (ml 20) and AcOEt (3×30 ml)
  4. customthe organic phases are collected

Sources & evidence

ORD record
ord-51111519c1874c0c8735f605cc74cf63
Source dataset
uspto-grants-1993_09
Patent number
US05245039

Reaction notes

Loading…