Ethyl Acetate → HCID 67583574, compound

HRID 1456547Notes

Reaction equation

HRID 1456547 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[CH:3]=1.CC(C)([O-])C.[K+].Cl[CH2:26][CH2:27][C@@H:28]1[CH2:32][C@@H:31]([OH:33])[CH2:30][N:29]1[C:34]([O:36][CH2:37][CH3:38])=[O:35].C(OCC)(=O)C>CN(C)C(=O)C>[CH2:37]([O:36][C:34]([N:29]1[CH2:30][C@H:31]([OH:33])[CH2:32][C@H:28]1[CH2:27][CH2:26][O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)=[O:35])[CH3:38]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 22106919HCID 22106919, compoundHCID 23665647Potassium tert-butoxideHCID 57273152HCID 57273152, compound

Product 1

HCID 67583574HCID 67583574, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
40 °C

Procedure

399 mg of 4-fluoro-2-[2-(3-methoxyphenyl)ethyl]phenol (prepared as described in Preparation 4) were dissolved in 8 ml of N,N-dimethylacetamide, and then 363 mg of potassium t-butoxide and 718 mg of (2S,4R)-2-(2-chloroethyl)-1-ethoxycarbonyl-4-hydroxypyrrolidine were added, whilst ice-cooling, to the resulting solution. The resulting mixture was then stirred at 40° C. for 5 hours. At the end of this time, 50 ml of ethyl acetate were added, and the reaction mixture was washed with water and with a saturated aqueous solution of sodium chloride, in that order. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and then concentrated by evaporation under reduced pressure. The resulting oily substance was purified by silica gel column chromatography, using a 3:7 by volume mixture of hexane and ethyl acetate as the eluent, to give 535 mg (yield 76%) of the title compound as a colorless oily substance.

Workup

  1. temperaturecooling, to the resulting solution
  2. washthe reaction mixture was washed with water and with a saturated aqueous solution of sodium chloride, in that order
  3. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe resulting oily substance was purified by silica gel column chromatography
  6. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-20c87aa4e11040889e879432d0ad32da
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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