Cyclopropane → HCID 86760504, compound

HRID 1294357Notes

Reaction equation

C1CC1.[C:4]([OH:14])(=[O:13])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[O:27]1[CH2:31][CH2:30][NH:29][C:28]1=[O:32]>>[C:4]([O-:14])(=[O:13])[CH:5]=[CH:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1.[O:27]1[CH2:31][CH2:30][NH:29][C:28]1=[O:32]

Participants

Reactant 4

HCID 6351Cyclopropane

HCID 87842-Propenoic acid, 3-phenyl-

HCID 682631,1'-Carbonyldiimidazole

HCID 739492-Oxazolidinone

Product 1

HCID 86760504HCID 86760504, compound

Procedure

Cis and trans chiral cyclopropane intermediates of type XIV and XVII respectively, can also be prepared by the following two methods. The cinnamic acid XIII in presence of CDI is converted to the acyl-imidazole XIX, which under basic condition reacts with the optically pure oxazolidinone XX to afford the chiral cinnamate-oxazolidinone XXI. Cyclopropanation of XXI following previously described method gives rise to a separable (crystallization, SiO2) mixture (>5 to 1) of diastereoisomers XXII. Hydrolysis of the latter will afford the desired chiral cyclopropyl XIV. Similarly, a racemic mixture of cyclopropyl of type XIV (XVII) can be converted in two steps to the 1:1 diastereoisomeric mixture of the previously described cinnamate-oxazolidinone XXI.

Sources & evidence

ORD record: ord-8fa985b786ff460bba59603661f3f6bc
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238706B2

Reaction notes

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