3-Nitrobenzaldehyde → 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3-(2-cyanoethyl) 5-methyl ester

HRID 846069

反応式

HRID 846069 の反応式
N12CCC(CC1)C(O)C2.[N+:10]([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O)([O-:12])=[O:11].[NH2:21]/[C:22](/[CH3:28])=[CH:23]\[C:24]([O:26][CH3:27])=[O:25].[C:29]([O:35][CH2:36][CH2:37][C:38]#[N:39])(=[O:34])[CH2:30][C:31]([CH3:33])=O>>[CH3:33][C:31]1[NH:21][C:22]([CH3:28])=[C:23]([C:24]([O:26][CH3:27])=[O:25])[CH:16]([C:15]2[CH:18]=[CH:19][CH:20]=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=2)[C:30]=1[C:29]([O:35][CH2:36][CH2:37][C:38]#[N:39])=[O:34]

参加物

5

反応物 4

HCID 74493-NitrobenzaldehydeHCID 15381(+-)-3-QuinuclidinolHCID 643918Methyl 3-aminocrotonateHCID 123604062-Cyanoethyl 3-oxobutanoate

生成物 1

HCID 109160093,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3-(2-cyanoethyl) 5-methyl ester

実験手順

The compounds of the invention can be prepared by esterification of the enantiomers of methyl 3-carboxy-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-5-pyridinedicarboxylate with the enantiomers of 1-azabicyclo[2.2.2]octan-3-ol (3-quinuclidinol). The acid may be prepared by condensation of 3-nitrobenzaldehyde with methyl 3-aminocrotonate and 2-cyanoethyl acetoacetate to afford 2-cyanoethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate which may be hydrolyzed with one equivalent of a suitable base (G.B. Patent 2122192), e.g. NaOH, to give methyl 3-carboxy-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-5-pyridinedicarboxylate. Resolution of the acid is achieved by recrystallization of the cinchonidine (U.S. Pat. No. 4,920,225) addition salt from ethanol free chloroform. The enantiomers of 3-quinuclidinol are obtained by the procedure of B. Ringdahl, B. Resul and R. Dahlbom (Acta. Pharm. Seuc., 1979, 16, 281).

出典と根拠

ORDレコード
ord-35fab266448d4adc8c98f2bff1e8404a
出典データセット
uspto-grants-1992_08
特許番号
US05135936

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