HCID 22106900, compound → HCID 54180348, compound

HRID 1456581Notes

Reaction equation

HRID 1456581 reaction equation
[CH3:1][O:2][C:3]1[C:8]([OH:9])=[C:7]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=1.CC(C)([O-])C.[K+].Cl[CH2:25][CH2:26][C@@H:27]1[CH2:31][C@@H:30]([O:32][C:33](=[O:37])[N:34]([CH3:36])[CH3:35])[CH2:29][N:28]1[C:38]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])=[O:39]>CN(C)C(=O)C>[CH3:35][N:34]([CH3:36])[C:33]([O:32][C@H:30]1[CH2:29][N:28]([C:38]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])=[O:39])[C@H:27]([CH2:26][CH2:25][O:9][C:8]2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=2[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:31]1)=[O:37]

Participants

5

Reactant 3

HCID 22106900HCID 22106900, compoundHCID 23665647Potassium tert-butoxideHCID 57115324HCID 57115324, compound

Product 1

HCID 54180348HCID 54180348, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

670 mg of 6-methoxy-2-(2-phenylethyl)phenol were dissolved in 10 ml of N,N-dimethylacetamide, allowed to react with 360 mg of potassium t-butoxide and 1000 mg of (2S,4R)-2-(2-chloroethyl)-4-dimethylcarbamoyloxy-1-octyloxycarbonylpyrrolidine 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 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1500 mg (99% yield) 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-91870e0b64cb41bda27d3a4c62c71185
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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