Dimethyl acetylenedicarboxylate → 3-(1-Pyrrolidinyl)-2,7-cycloheptadiene-1,2-dicarboxylic acid, dimethyl ester

HRID 615342Notes

Reaction equation

[C:1]1([N:6]2[CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH:2]=1.[C:11]([O:19][CH3:20])(=[O:18])[C:12]#[C:13][C:14]([O:16][CH3:17])=[O:15]>>[N:6]1([C:1]2[CH2:5][CH2:4][CH2:3][CH:2]=[C:13]([C:14]([O:16][CH3:17])=[O:15])[C:12]=2[C:11]([O:19][CH3:20])=[O:18])[CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylate

HCID 81570Pyrrolidine, 1-(1-cyclopenten-1-yl)-

Product 1

HCID 124045193-(1-Pyrrolidinyl)-2,7-cycloheptadiene-1,2-dicarboxylic acid, dimethyl ester

Procedure

1-(1-Cyclopenten-1-yl)pyrrolidine and 2-butynedioic acid, dimethyl ester are reacted according to the procedure set forth in J.O.C., Vol. 28, p. 1464 (1963) to yield 3-(1-pyrrolidinyl)-2,7-cycloheptadiene-1,2-dicarboxylic acid, dimethyl ester.

Sources & evidence

ORD record: ord-e6d9da2b50e54eb7a21c3f62ff2ee73b
Source dataset: uspto-grants-1985_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04499079

Reaction notes

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