HCID 22107008, compound → HCID 54022454, compound

HRID 1456568Notes

Reaction equation

HRID 1456568 reaction equation
[CH3:1][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]=[CH:13][CH:12]=2)[CH:3]=1.CC(C)([O-])C.[K+].[CH2:23]([O:30][C@H:31]1[CH2:35][N:34]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[C@H:33]([CH2:41][CH2:42]Cl)[CH2:32]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C(=O)C>[CH2:39]([O:38][C:36]([N:34]1[CH2:35][C@H:31]([O:30][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:32][C@H:33]1[CH2:41][CH2:42][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][C:4]=1[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:37])[CH3:40]

Participants

5

Reactant 3

HCID 22107008HCID 22107008, compoundHCID 23665647Potassium tert-butoxideHCID 57237055HCID 57237055, compound

Product 1

HCID 54022454HCID 54022454, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

1200 mg of 4-methyl-2-(2-phenylethyl)phenol were dissolved in 10 ml of N,N-dimethylacetamide, allowed to react with 700 mg of potassium t-butoxide and 1600 mg of (2S,4R)-4-benzyloxy-2-(2-chloroethyl)-1-ethoxycarbonylpyrrolidine 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 3:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1820 mg (yield 73%) 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-b27d6d7b411141d789cf19179c6dd833
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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