HCID 13663160, compound → HCID 13663197, compound

HRID 1589642Notes

Reaction equation

HRID 1589642 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[CH2:7]([N:14]([CH2:16][CH2:17][O:18][CH2:19][C:20]1[NH:21][C:22]([CH3:42])=[C:23]([C:38]([O:40][CH3:41])=[O:39])[CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[Cl:37])[C:25]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27])C)C1C=CC=CC=1>CO.[Pd]>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[Cl:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[CH:24]1[C:23]([C:38]([O:40][CH3:41])=[O:39])=[C:22]([CH3:42])[NH:21][C:20]([CH2:19][O:18][CH2:17][CH2:16][NH:14][CH3:7])=[C:25]1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

4

Reactant 1

HCID 13663160HCID 13663160, compound

Product 1

HCID 13663197HCID 13663197, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A solution of 2-[2-(N-benzyl-N-methylamino)ethoxymethyl]-4-[2-chlorophenyl]-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine, oxalate salt (4.3 g) in methanol (220 ml) was added to a suspension of 10% (by weight) palladium on charcoal (0.4 g) pre-hydrogenated in methanol (50 ml). Stirring under hydrogen at 50 p.s.i. and room temperature overnight resulted in complete removal of the benzyl group. After removal of the catalyst by filtration, the methanol was removed by evaporation and the residue crystallised from a little methanol to give the title compound (2.4 g), m.p. 211°.

Workup

  1. customand room temperature overnight resulted in complete removal of the benzyl group
  2. customAfter removal of the catalyst
  3. filtrationby filtration
  4. customthe methanol was removed by evaporation
  5. customthe residue crystallised from a little methanol

Sources & evidence

ORD record
ord-28c219e294be4df3bb95894b21678112
Source dataset
uspto-grants-1986_02
Patent number
US04572909

Reaction notes

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