Dicyclohexylcarbodiimide → Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaS)-

HRID 1090618Notes

Reaction equation

HRID 1090618 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH3:16][C:17]1([CH3:33])[CH:19]([CH:20]([O:25][S:26]([CH3:29])(=[O:28])=[O:27])[C:21]([Br:24])([Br:23])[Br:22])[CH:18]1[C:30]([OH:32])=[O:31].[C:34]([CH:36]([OH:50])[C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([O:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:38]=1)#[N:35]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:34]([CH:36]([OH:50])[C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([O:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:38]=1)#[N:35].[CH3:16][C:17]1([CH3:33])[CH:19]([CH:20]([O:25][S:26]([CH3:29])(=[O:28])=[O:27])[C:21]([Br:23])([Br:24])[Br:22])[CH:18]1[C:30]([O-:32])=[O:31]

Participants

7

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 93218Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaS)-2×HCID 19796903HCID 19796903, compound

Product 2

HCID 93218Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaS)-HCID 19796902HCID 19796902, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

0.78 g of dicyclohexylcarbodiimide and 3 ml of methylene chloride were added to a solution of 1.8 g of the product of Step C, 20 ml of methylene chloride, 0.86 g of (S) α-cyano-3-phenoxy-benzyl alcohol and 0.1 g of 4-dimethylamino-pyridine. The mixture was stirred at 20° to 25° C. for 2 hours and the product formed was dried and the filtrate was evaporated to dryness under reduced pressure. A chromatography was carried out with elution with a hexane-ethyl acetate mixture (7-3) to obtain 2 g of α-cyano-3-phenoxy-benzyl 1R-[1α(S) 3α (S)] 2,2-dimethyl-3-[2,2,2-tribromo-1-methylsulfonyloxyethyl]-cyclopropane carboxylate with a specific rotation [α]D20 =1°±1° (c=1% in CHCl3).

Workup

  1. customthe product formed
  2. customwas dried
  3. customthe filtrate was evaporated to dryness under reduced pressure
  4. washA chromatography was carried out with elution with a hexane-ethyl acetate mixture (7-3)

Sources & evidence

ORD record
ord-51975247214042a2ad2053dd0570a488
Source dataset
uspto-grants-1992_01
Patent number
US05082832

Reaction notes

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