Hydrochloric Acid → (1R,2S)-1-cyano-2-hexyl-1-[4-{4-(4-octyloxyphenyl)phenylmethoxy}phenyl]cyclopropane

HRID 973520Notes

Reaction equation

HRID 973520 reaction equation
[C:1]([C@:3]1([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[CH2:5][C@@H:4]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])#[N:2].CC(C)([O-])C.[K+].[CH2:25]([O:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:47]=[CH:46][C:43]([CH2:44]Br)=[CH:42][CH:41]=2)=[CH:36][CH:35]=1)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].Cl>CN(C=O)C>[C:1]([C@:3]1([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:44][C:43]3[CH:42]=[CH:41][C:40]([C:37]4[CH:38]=[CH:39][C:34]([O:33][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:35][CH:36]=4)=[CH:47][CH:46]=3)=[CH:16][CH:17]=2)[CH2:5][C@@H:4]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 147458854-(4-Octyloxyphenyl)benzyl bromideHCID 15733984(1R,2S)-1-cyano-2-hexyl-1-(4-hydroxyphenyl)cyclopropaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 57075108(1R,2S)-1-cyano-2-hexyl-1-[4-{4-(4-octyloxyphenyl)phenylmethoxy}phenyl]cyclopropaneYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In 10 ml of DMF was dissolved 49 mg of (1R,2S)-1-cyano-2-hexyl-1-(4-hydroxyphenyl)cyclopropane as obtained in Example 11. Thereto was added 34 mg of potassium t-butoxide, and the resulting mixture was stirred at room temperature for 70 minutes. Thereto was added dropwise a solution of 98 mg of 4-(4-octyloxyphenyl)benzyl bromide in 3 ml of DMF, and this mixture was stirred for 6 hours. Thereafter, 20 ml of 5% hydrochloric acid was added to the reaction mixture, and the resulting mixture was subjected to extraction with 50 ml of ether. The resulting organic layer was washed with water and then with saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. The solvent was removed by evaporation and the residue was purified by silica gel column chromatography (solvent: hexane/ethyl acetate=10/1), thereby obtaining 103 mg of the desired compound in the form of white crystals.

Workup

  1. customas obtained in Example 11
  2. stirringthis mixture was stirred for 6 hours
  3. extractionthe resulting mixture was subjected to extraction with 50 ml of ether
  4. washThe resulting organic layer was washed with water
  5. dry with materialwith saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate
  6. customThe solvent was removed by evaporation
  7. customthe residue was purified by silica gel column chromatography (solvent: hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-b633c4b865994953ba00d6d55dcd7b37
Source dataset
uspto-grants-1991_11
Patent number
US05064564

Reaction notes

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