2-(4-Phenylbutyl)phenol → (4R)-4-Benzyloxy-1-t-butoxycarbonyl-2-[2-(4-phenylbutyl) phenoxymethyl]pyrrolidine

HRID 743242Notes

Reaction equation

HRID 743242 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[CH2:24]([O:31][C@H:32]1[CH2:36][N:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH:34]([CH2:44]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:33]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CC(N(C)C)=O>[CH2:24]([O:31][C@H:32]1[CH2:36][N:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH:34]([CH2:44][O:17][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:33]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 125964892-(4-Phenylbutyl)phenolHCID 23665647Potassium tert-butoxideHCID 53856550(4R)-4-benzyloxy-1-t-butoxycarbonyl-2-(p-toluenesulfonyloxymethyl)pyrrolidine

Product 1

HCID 54385681(4R)-4-Benzyloxy-1-t-butoxycarbonyl-2-[2-(4-phenylbutyl) phenoxymethyl]pyrrolidineYield 24.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
40 °C

Procedure

441 mg of 2-(4-phenylbutyl)phenol (prepared as described in Preparation 3) and 241 mg of potassium t-butoxide were dissolved, with ice-cooling and stirring, in 20 ml of dimethylacetamide. 900 mg of (4R)-4-benzyloxy-1-t-butoxycarbonyl-2-(p-toluenesulfonyloxymethyl)pyrrolidine were then added to the solution thus obtained, and the resulting mixture was stirred at 40° C. for 5 hours. At the end of this time, the reaction mixture was cooled and partitioned between ethyl acetate and water. The organic layer was dried over anhydrous sodium sulfate, and concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel, using a 4:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 242 mg (yield 24%) of the title compound as a colorless oil.

Workup

  1. temperaturecooling
  2. customthus obtained
  3. temperatureAt the end of this time, the reaction mixture was cooled
  4. custompartitioned between ethyl acetate and water
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe residue was purified by column chromatography through silica gel
  8. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-ff2566da914b45f0b68d997e5fe8bd93
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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