Pyridine → HCID 86739796, compound

HRID 1154398Notes

Reaction equation

HRID 1154398 reaction equation
N1C=CC=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:22][C:23]1([CH3:38])[C@@H:25](/[CH:26]=[C:27](\[Br:34])/[C:28]([O:30][CH2:31][CH2:32][CH3:33])=[O:29])[C@H:24]1[C:35]([OH:37])=[O:36].[C:39]([C@@H:41](O)[C:42]1[CH:47]=[CH:46][CH:45]=[C:44]([O:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH:43]=1)#[N:40]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:38][C:23]1([CH3:22])[C@@H:25](/[CH:26]=[C:27](\[Br:34])/[C:28]([O:30][CH2:31][CH2:32][CH3:33])=[O:29])[C@H:24]1[C:35]([O:37][C@H:41]([C:39]#[N:40])[C:42]1[CH:47]=[CH:46][CH:45]=[C:44]([O:48][C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH:43]=1)=[O:36]

Participants

7

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 9837437(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrileHCID 86739797HCID 86739797, compound

Product 1

HCID 86739796HCID 86739796, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

0.9 ml of pyridine and 2.1 g of dicyclohexylcarbodiimide were added to a solution of 2.9 g of the product of Step B in 40 ml of methylene chloride and the mixture was stirred for 15 minutes. A solution of 2.5 g of (S)α-cyano-3-phenoxy-benzyl alcohol in 15 ml of methylene chloride and then 25 mg of 4-dimethylamino-pyridine were added to the reaction mixture which was stirred for 2 hours and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a 9-1 cyclohexane-ethyl acetate mixture yielded 4.26 g of (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3(Z)-[2-bromo-2-propoxycarbonyl-ethenyl]-cyclopropane-1-carboxylate melting at 64° C.

Workup

  1. stirringwas stirred for 2 hours
  2. filtrationfiltered
  3. customThe filtrate was evaporated to dryness under reduced pressure
  4. customthe residue was chromatographed over silica gel
  5. washElution with a 9-1 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-e3989a5f1f9b4a9889e15b00ebec372f
Source dataset
uspto-grants-1984_12
Patent number
US04489093

Reaction notes

Loading…