HCID 22106926, compound → HCID 67584131, compound

HRID 1456552Notes

Reaction equation

HRID 1456552 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][C:14]([F:17])=[C:13]([O:18][CH3:19])[CH:12]=2)[CH:3]=1.CC(C)([O-])C.[K+].Cl[CH2:27][CH2:28][C@@H:29]1[CH2:33][C@@H:32]([OH:34])[CH2:31][N:30]1[C:35]([O:37][CH2:38][CH3:39])=[O:36]>CN(C)C(=O)C>[CH2:38]([O:37][C:35]([N:30]1[CH2:31][C@H:32]([OH:34])[CH2:33][C@H:29]1[CH2:28][CH2:27][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][C:14]([F:17])=[C:13]([O:18][CH3:19])[CH:12]=1)=[O:36])[CH3:39]

Participants

5

Reactant 3

HCID 22106926HCID 22106926, compoundHCID 23665647Potassium tert-butoxideHCID 57273152HCID 57273152, compound

Product 1

HCID 67584131HCID 67584131, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

622 mg of 4-fluoro-2-[2-(4-fluoro-3-methoxyphenyl)ethyl]phenol (prepared as described in Preparation 5) were dissolved in 7 ml of N,N-dimethylacetamide. The resulting solution was allowed to react with 343 mg of potassium t-butoxide and 678 mg of (2S,4R)-2-(2-chloroethyl)-1-ethoxycarbonyl-4-hydroxypyrrolidine and extracted in the same manner as described in step (a) of Example 1. The resulting oily substance was purified by silica gel column chromatography, using a 2:3 by volume mixture of hexane and ethyl acetate as the eluent, to give 552 mg (yield 52%) of the title compound as a colorless oily substance.

Workup

  1. extractionextracted in the same manner
  2. customThe resulting oily substance was purified by silica gel column chromatography
  3. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-923f15e7de2d4c6ebd843f754651f371
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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