Dicyclohexylcarbodiimide → (RS)1-(6-phenoxy-2-pyridyl)-ethyl(1R,cis,Z)2,2-dimethyl-3-[3-oxo-3-tert.-butoxy-1-propenyl]-cyclopropane-carboxylate

HRID 1639458Notes

Reaction equation

C1(N=C=NC2CCCCC2)CCCCC1.[CH3:16][C:17]1([CH3:32])[C@@H:19](/[CH:20]=[CH:21]\[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C@H:18]1[C:29]([OH:31])=[O:30].[O:33]([C:40]1[N:45]=[C:44]([CH:46](O)[CH3:47])[CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:16][C:17]1([CH3:32])[C@@H:19](/[CH:20]=[CH:21]\[C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[C@H:18]1[C:29]([O:31][CH:46]([C:44]1[CH:43]=[CH:42][CH:41]=[C:40]([O:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:45]=1)[CH3:47])=[O:30]

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 55.7 g of dicyclohexylcarbodiimide, 2.6 g of 4-dimethylamino-pyridine and 450 ml of methylene chloride were added over 25 minutes at 0° C. to a mixture of 65 g of (1R,cis,Z) 2,2-dimethyl-3-[3-oxo-3-tert.-butoxy-1-propenyl]-cyclopropane-carboxylic acid, 70 g of (RS) 1-(6-phenoxy-2-pyridyl)-ethanol and 650 ml of methylene chloride and the mixture was stirred at 20° C. for 4 hours and was vacuum filtered. The filtrate was evaporated to dryness and the residue was chromatographed over silica gel. Elution with an 100-4 n-hexane-ethyl acetate mixture yielded 101 g of (RS) 1-(6-phenoxy-2-pyridyl)-ethyl (1R,cis,Z) 2,2-dimethyl-3-[3-oxo-3-tert.-butoxy-1-propenyl]-cyclopropane-carboxylate with a specific rotation of [αD20 =+64° (c=1% in toluene).

Workup

filtrationfiltered
customThe filtrate was evaporated to dryness
customthe residue was chromatographed over silica gel
washElution with an 100-4 n-hexane-ethyl acetate mixture

Sources & evidence

ORD record: ord-454ed0ed5ead49c5a65f7064dca75aef
Source dataset: uspto-grants-1989_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04883806

Reaction notes

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