Pyridine → 4-((1R,2S)-1-cyano-2-hexylcyclopropyl)phenyl (S)-4-[4-(2-propoxypropanoyloxy)phenyl]benzoate

HRID 973521Notes

Reaction equation

HRID 973521 reaction equation
[CH2:1]([O:4][C@@H:5]([CH3:24])[C:6]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)=[O:7])[CH2:2][CH3:3].[C:25]([C@:27]1([C:36]2[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=2)[CH2:29][C@@H:28]1[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])#[N:26].N1C=CC=CC=1.CCOCC>ClCCl>[CH2:1]([O:4][C@@H:5]([CH3:24])[C:6]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([O:42][C:39]3[CH:38]=[CH:37][C:36]([C@@:27]4([C:25]#[N:26])[CH2:29][C@@H:28]4[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:41][CH:40]=3)=[O:20])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)=[O:7])[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 14573372(S)-4-[4-(2-propoxypropanoyloxy)phenyl]benzoyl chlorideHCID 15733984(1R,2S)-1-cyano-2-hexyl-1-(4-hydroxyphenyl)cyclopropane

Product 1

HCID 157339934-((1R,2S)-1-cyano-2-hexylcyclopropyl)phenyl (S)-4-[4-(2-propoxypropanoyloxy)phenyl]benzoateYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 10 ml of dichloromethane were dissolved 83 mg of (S)-4-[4-(2-propoxypropanoyloxy)phenyl]benzoyl chloride and 65 mg of (1R,2S)-1-cyano-2-hexyl-1-(4-hydroxyphenyl)cyclopropane. To this solution was added 0.5 ml of pyridine. The resulting mixture was stirred for 3 hours under reflux. The reaction mixture was cooled, and then ether was added thereto. The ethanol phase was separated, washed with diluted hydrochloric acid, water, and then 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=5/1). Recrystallization from ethanol afforded, thereby obtaining 61 mg of the desired compound as colorless crystals.

Workup

  1. temperatureunder reflux
  2. temperatureThe reaction mixture was cooled
  3. customThe ethanol phase was separated
  4. washwashed with diluted hydrochloric acid, water
  5. dry with materialsaturated 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=5/1)
  8. customRecrystallization from ethanol
  9. customafforded

Sources & evidence

ORD record
ord-276cbc39877e44178f957c4dbba6edec
Source dataset
uspto-grants-1991_11
Patent number
US05064564

Reaction notes

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