Carbamimidic acid, N,N'-bis(1-methylethyl)-, 1-methylethyl ester → tert.-butyl(1R,cis)2,2-dimethyl-3-[Z-2-(isopropoxycarbonyl)-ethenyl]-cyclopropane-carboxylate
Reaction equation
[CH:1](OC(=NC(C)C)NC(C)C)([CH3:3])[CH3:2].[CH3:14][C:15]1([CH3:30])[C@@H:17](/[CH:18]=[CH:19]\[C:20]([OH:22])=[O:21])[C@H:16]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]>C(OCC)(=O)C>[CH3:14][C:15]1([CH3:30])[C@@H:17](/[CH:18]=[CH:19]\[C:20]([O:22][CH:1]([CH3:3])[CH3:2])=[O:21])[C@H:16]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2 g of O-isopropyl-N,N'-diisopropyl-isourea were added to a mixture of 2.7 g of the product of Step A and 10 ml of ethyl acetate and the mixture was stirred at room temperature for one hour, refluxed for 90 minutes and then cooled to 20° C. The mixture was filtered and the filtrate was evaporated to dryness under reduced pressure. The 3.5 g of oil residue were chromatographed over silica gel and eluted with a 7-3 benzene-cyclohexane mixture to obtain 1 g of tert.-butyl(1R,cis)2,2-dimethyl-3-[Z-2-(isopropoxycarbonyl)-ethenyl]-cyclopropane-carboxylate which was used as is for the next step.
Workup
- temperaturerefluxed for 90 minutes
- temperaturecooled to 20° C
- filtrationThe mixture was filtered
- customthe filtrate was evaporated to dryness under reduced pressure
- customThe 3.5 g of oil residue were chromatographed over silica gel
- washeluted with a 7-3 benzene-cyclohexane mixture
Sources & evidence
- ORD record
- ord-b8b1581900384123aa92dcf9829164f4
- Source dataset
- uspto-grants-1985_10
- Patent number
- US04547522
Reaction notes
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