Ammonia → 3-cyclopropylmethyl 5-[2-(N-methyl-N-trimethylsilylmethylamino)ethyl] 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate

HRID 621541Notes

Reaction equation

HRID 621541 reaction equation
[C:1]([O:7][CH2:8][CH2:9][N:10]([CH3:16])[CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[N+:17]([C:20]1[CH:21]=[C:22]([CH:35]=[CH:36][CH:37]=1)[CH:23]=[C:24]([C:32]([CH3:34])=O)[C:25]([O:27][CH2:28][CH:29]1[CH2:31][CH2:30]1)=[O:26])([O-:19])=[O:18].[NH3:38]>C(O)C>[CH3:34][C:32]1[NH:38][C:3]([CH3:5])=[C:2]([C:1]([O:7][CH2:8][CH2:9][N:10]([CH3:16])[CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])=[O:6])[CH:23]([C:22]2[CH:35]=[CH:36][CH:37]=[C:20]([N+:17]([O-:19])=[O:18])[CH:21]=2)[C:24]=1[C:25]([O:27][CH2:28][CH:29]1[CH2:31][CH2:30]1)=[O:26]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 212433402-(N-methyl-N-trimethylsilylmethylamino)ethyl acetoacetateHCID 53956239Cyclopropylmethyl 2-(3-nitrobenzylidene)acetoacetate

Product 1

HCID 141000963-cyclopropylmethyl 5-[2-(N-methyl-N-trimethylsilylmethylamino)ethyl] 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylateYield 25.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 15.3 g (53 mmol) of 2-(N-methyl-N-trimethylsilylmethylamino)ethyl acetoacetate, 13.0 g (53 mmol) of cyclopropylmethyl 2-(3-nitrobenzylidene)acetoacetate, 4.4 ml of 28% aqueous ammonia and 50 ml of ethanol was stirred at the reflux temperature for 7 hours, and then the solvent was removed under reduced pressure. The residue was chromatographed on silica gel column to afford 3-cyclopropylmethyl 5-[2-(N-methyl-N-trimethylsilylmethylamino)ethyl] 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate (7.0 g, 25.7%) as yellow oil. Treatment of this oil with 1 equivalent of fumaric acid in ethanol gave the corresponding fumarate.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was chromatographed on silica gel column

Sources & evidence

ORD record
ord-c949359ff57f46b29008d9dee23b3171
Source dataset
uspto-grants-1989_04
Patent number
US04824855

Reaction notes

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