Distannoxane, 1,1,3,3-tetrabutyl-1,3-dichloro- → 3-chloro-6-cyclopentyl-6-[2-(3-fluoro-4-isopropoxyphenyl)ethyl]-4-hydroxy-5,6-dihydro-2H-pyran-2-one

HRID 858821Notes

Reaction equation

HRID 858821 reaction equation
[Cl:1][CH:2]([C:7](=[O:29])[CH2:8][C:9]([CH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1)(O)[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH:19]([CH3:21])[CH3:20])=[C:14]([F:22])[CH:13]=1)[C:3]([O:5]C)=[O:4].CCCC[Sn](Cl)(O[Sn](Cl)(CCCC)CCCC)CCCC>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3](=[O:4])[O:5][C:9]([CH:24]2[CH2:25][CH2:26][CH2:27][CH2:28]2)([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH:19]([CH3:21])[CH3:20])=[C:14]([F:22])[CH:13]=2)[CH2:8][C:7]=1[OH:29]

Participants

4

Reactant 2

HCID 16682755Distannoxane, 1,1,3,3-tetrabutyl-1,3-dichloro-HCID 58762410Methyl 2-chloro-5-cyclopentyl-7-(3-fluoro-4-isopropoxyphenyl)-5-hydroxy-3-oxoheptanoate

Product 1

HCID 587627503-chloro-6-cyclopentyl-6-[2-(3-fluoro-4-isopropoxyphenyl)ethyl]-4-hydroxy-5,6-dihydro-2H-pyran-2-oneYield 50%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of methyl 2-chloro-5-cyclopentyl-7-(3-fluoro-4-isopropoxyphenyl)-5-hydroxy-3-oxoheptanoate (1.74 g, 4.1 mmol), and bis(dibutylchlorotin)oxide (1.38 g, 2.5 mmol), dissolved in toluene (20 mL) were heated at reflux for 30 mins. The resulting mixture was concentrated and purified by silica gel chromatography to give the title compound (0.80 g, 50% yield, two Steps).

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 30 mins
  3. concentrationThe resulting mixture was concentrated
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-5298e9340e794ffe8e31696e3562e0f3
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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