2,6-Dimethyl-3-cyclopentyloxycarbonyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid benzyl ester → (Z)-Benzyl 3-aminobut-2-enoate

HRID 442179Notes

Reaction equation

HRID 442179 reaction equation
[CH2:1]([O:8][C:9]([C:11]1C(C2C=CC=CC=2[N+]([O-])=O)C(C(OC2CCCC2)=O)=C(C)[NH:15][C:16]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C>[CH2:1]([O:8][C:9](=[O:10])/[CH:11]=[C:16](\[NH2:15])/[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 681227152,6-Dimethyl-3-cyclopentyloxycarbonyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid benzyl ester

Product 1

HCID 5368345(Z)-Benzyl 3-aminobut-2-enoateYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Analogously to Example 1 heating a solution of 75 mmols of 2'-nitrobenzylideneacetoacetic acid cyclopentyl ester and 75 mmols of β-aminocrotonic acid benzyl ester in 120 ml of ethanol gave 2,6-dimethyl-3-cyclopentyloxycarbonyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid benzyl ester of melting point 111° C (from ethanol).

Sources & evidence

ORD record
ord-8be592fc8f36496e934a52e2572cd0cc
Source dataset
uspto-grants-1977_08
Patent number
US04044141

Reaction notes

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