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 1453277Notes

Reaction equation

HRID 1453277 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). 1H NMR (300 MHz, CDCl3): δ 1.33 (d, J=6.03 Hz, 6H), 1.45-1.80 (m, 10H), 1.99-2.05 (m, 2H), 2.34-2.44 (m, 1H), 2.59-2.66 (m, 2H), 4.44-4.52 (m, 1H), 6.78-6.91 (m, 3H).

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-5d153ec630444f0b992ff546f637827b
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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