HCID 14531142, compound → HCID 54078194, compound

HRID 1456575Notes

Reaction equation

HRID 1456575 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:4]=1.CC(C)([O-])C.[K+].Cl[CH2:25][CH2:26][C@@H:27]1[CH2:31][C@@H:30]([OH:32])[CH2:29][N:28]1[C:33]([O:35][CH2:36][CH3:37])=[O:34]>CN(C)C(=O)C>[CH2:36]([O:35][C:33]([N:28]1[CH2:29][C@H:30]([OH:32])[CH2:31][C@H:27]1[CH2:26][CH2:25][O:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:34])[CH3:37]

Participants

5

Reactant 3

HCID 14531142HCID 14531142, compoundHCID 23665647Potassium tert-butoxideHCID 57273152HCID 57273152, compound

Product 1

HCID 54078194HCID 54078194, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

1130 mg of 4-methoxy-2-(2-phenylethyl)phenol were dissolved in 10 ml of N,N-dimethylacetamide, allowed to react with 610 mg of potassium t-butoxide and 1000 mg of (2S,4R)-2-(2-chloroethyl)-1-ethoxycarbonyl-4-hydroxypyrrolidine and extracted in the same manner as described in step (a) of Example 2. The resulting oily substance was purified by silica gel column chromatography, using a 1:2 by volume mixture of hexane and ethyl acetate as the eluent, to give 448 mg (yield 24%) of the title compound as an 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-396e9a000bb743b69589b426f9fe6324
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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