(Ethylsulphonyl)benzene → 4-Benzenesulfonyl-3-methylpentanoic acid methyl ester

A solution of n-butyllithium in hexanes (7.48 ml, 11.22 mmol) was added dropwise to a stirred solution of ethyl phenyl sulphone (1.87 g, 11 mmol) in THF (25 ml) at −78° C. The mixture was stirred for 30 min. and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (1.5 ml, 12.43 mmol) was added followed by methyl crotonate (2.0 ml, 18.7 mmol). The reaction mixture was stirred for 90 min., quenched with sat. aqueous NH4Cl and extracted into ethyl acetate. The organic extract was dried (Na2SO4) and concentrated to give 4-benzenesulfonyl-3-methylpentanoic acid methyl ester as a 8:1 mixture of diastereoisomers that was dissolved in dichloromethane (20 ml) and cooled using a ice-bath. A solution of diisobutyl aluminium hydride in dichloromethane (50.0 ml, 50.0 mmol) was added and the reaction mixture was stirred at room temperature for 30 min. Ethyl acetate (10 ml) was added and the resulting mixture was poured into dichloromethane (200 ml) and cooled with an ice-bath. Water (4 ml) was added dropwise and the mixture was stirred for 30 min. dried over Na2SO4 for 30 min. filtered through a pad of Celite and concentrated. The residue was purified on silica gel (i-hexane-ethyl acetate) to give the title product.

1. stirringThe reaction mixture was stirred for 90 min.
2. customquenched with sat. aqueous NH4Cl
3. extractionextracted into ethyl acetate
4. extractionThe organic extract
5. dry with materialwas dried (Na2SO4)
6. concentrationconcentrated

ORD record

ord-9a817564b1394b2fb3a5837c0724d4ab

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07101892B2