4-Toluenesulfonyl chloride → (R)-Toluene-4-sulfonic acid 3-benzyloxymethoxy-2-methyl-propyl ester

To a mixture of diol 3 (29.2 mmol, 6.13 g), DMAP (0.82 mmol, 100 mg) and triethylamine (116.7 mmol, 16.2 mL, 11.8 g) in anhydrous CH2Cl2 (60 mL) was added tosyl chloride (37.9 mmol, 7.23 g) at 0° C. The reaction mixture was allowed to warm to room temperature and stirring was continued overnight. The mixture was then diluted with CH2Cl2 (100 mL) and was then washed with a saturated aqueous solution of NaHCO3, dried over Na2SO4, and concentrated under reduced pressure. The residue was chromatographed on a silica gel using hexane/EtOAc (7:3) as an eluent to give the oily tosylate 4 (10.2 g, 97%).

1. washwas then washed with a saturated aqueous solution of NaHCO3
2. dry with materialdried over Na2SO4
3. concentrationconcentrated under reduced pressure
4. customThe residue was chromatographed on a silica gel

ORD-Eintrag

ord-90137c7ce6f347fcb8691c1e954ae976

Quelldatensatz

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07534777B2