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

HRID 621541ノート

反応式

HRID 621541 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-c949359ff57f46b29008d9dee23b3171
出典データセット
uspto-grants-1989_04
特許番号
US04824855

反応ノート

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