Carbon Dioxide → HCID 22335624, compound

HRID 586626Notes

Reaction equation

C([CH2:4][C:5]1[N:12]2[C:8]([CH2:9][CH2:10][CH2:11]2)=[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:6]=1[C:19]1(C(O)=O)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)(O)=O.C(=O)=O.C(OC(C)C)(C)C>>[CH:19]1([C:6]2[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:8]3[N:12]([CH2:11][CH2:10][CH2:9]3)[C:5]=2[CH3:4])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

Reactant 3

HCID 280Carbon Dioxide

HCID 7914Diisopropyl Ether

HCID 22335650HCID 22335650, compound

Product 1

HCID 22335624HCID 22335624, compound

Procedure

1-(3-Carboxymethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-2-yl)cyclohexanecarboxylic acid (1.5 g, 3.7 mmol) is immersed in an oil bath of 150° C. for 30 min in a 25 ml flask. The release of CO2 is checked via a bubble counter. The still warm melt is digested with diisopropyl ether (15 ml). The insoluble crystalline residue is filtered off with suction and dried. 0.84 g (82% of theory) of decarboxylation product 6-cyclohexyl-5-methyl-7-phenyl-2,3-dihydro-1H-pyrrolizine (TLC: SiO2, ether-n-hexane (1:1): starting material Rf 0-0.2, product 0.9) is obtained.

Workup

filtrationThe insoluble crystalline residue is filtered off with suction
customdried

Sources & evidence

ORD record: ord-349a11e28f1543d6b5805494fb263d58
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06936632B2

Reaction notes

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