Cyclopropane → HCID 86760504, compound

HRID 1392689Notes

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-4f9107ed882d4f5981f4795d194f8f24
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07342024B2

Reaction notes

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