1,2-Dimethoxyethane → 7-{(R)-2-[(E)-3-(3-benzyl-phenyl)-3-hydroxy-propenyl]-5-oxo-pyrrolidin-1-yl}-heptanoic acid ethyl ester

HRID 2184327Notes

Reaction equation

HRID 2184327 reaction equation
[H-].[Na+].COCCOC.COP([CH2:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:19]=1)=[O:17])(=O)OC.[CH2:31]([O:33][C:34](=[O:49])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][N:41]1[C:45](=[O:46])[CH2:44][CH2:43][C@@H:42]1[CH:47]=O)[CH3:32]>C(OCC)(=O)C>[CH2:31]([O:33][C:34](=[O:49])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][N:41]1[C:45](=[O:46])[CH2:44][CH2:43][C@@H:42]1/[CH:47]=[CH:15]/[CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:19]=1)[OH:17])[CH3:32]

Participants

6

Reactant 4

HCID 80711,2-Dimethoxyethane2×HCID 24758Sodium hydrideHCID 112656767-((R)-2-formyl-5-oxo-pyrrolidin-1-yl)-heptanoic acid ethyl esterHCID 11359040[2-(3-Benzyl-phenyl)-2-oxo-ethyl]-phosphonic acid dimethyl ester

Product 1

HCID 695472897-{(R)-2-[(E)-3-(3-benzyl-phenyl)-3-hydroxy-propenyl]-5-oxo-pyrrolidin-1-yl}-heptanoic acid ethyl esterYield 51.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 60% sodium hydride in mineral oil (20 mg, 0.51 mmol) was added a DME solution (5 mL) of [2-(3-benzyl-phenyl)-2-oxo-ethyl]-phosphonic acid dimethyl ester (164 mg, 0.51 mmol). After 1.5 h a DME solution (5 mL) of 7-((R)-2-formyl-5-oxo-pyrrolidin-1-yl)-heptanoic acid ethyl ester (126 mg, 0.47 mmol) was added. The reaction mixture was stirred for 45 min. at room temperature then diluted with ethyl acetate and washed with an aqueous NaHCO3 solution. The organic layer was dried over MgSO4, filtered and concentrated. The residue was subjected to column chromatography (2.5 ethyl acetate: 1 hexanes) to provide 7-{(R)-2-[(E)-3-(3-benzyl-phenyl)-3-hydroxy-propenyl]-5-oxo-pyrrolidin-1-yl}-heptanoic acid ethyl ester (112 mg, 0.24 mmol) as an oil.

Workup

  1. washwashed with an aqueous NaHCO3 solution
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0bcfde7a59a64a06a64e1acd6f511e60
Source dataset
uspto-grants-2005_05
Patent number
US06900336B2

Reaction notes

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