HCID 21840937, compound → HCID 54414263, compound

HRID 1456571Notes

Reaction equation

HRID 1456571 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[CH:4][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:7]1[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]=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 21840937HCID 21840937, compoundHCID 23665647Potassium tert-butoxideHCID 57237055HCID 57237055, compound

Product 1

HCID 54414263HCID 54414263, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

1200 mg of 6-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 2260 mg (yield 90%) 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-ab10e164da2649cf9cbf912e697b3039
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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