Reaction #67292

ord-f2081859b3ba465aae8f87e4b3bf260f

Reaction equation

O=S(=O)(c1ccc2c(c1)OC(CO)CO2)C(F)(F)F
[7-(trifluoromethylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methanol
Cc1ccccc1S(=O)(=O)Cl
toluenesulfonyl chloride
ClCCl
DCM
→
Cc1ccc(S(=O)(=O)OC[C@H]2COc3ccc(S(=O)(=O)C(F)(F)F)cc3O2)cc1
[(2R)-7-(TRIFLUOROMETHYLSULFONYL)-2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL]METHYL 4-METHYLBENZENESULFONATE

Reactants

—
( 41 )
—
( 80 )
—
( 84 )
—
TEA
O=S(=O)(c1ccc2c(c1)OC(CO)CO2)C(F)(F)F
[7-(trifluoromethylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methanol
Cc1ccccc1S(=O)(=O)Cl
toluenesulfonyl chloride
ClCCl
DCM
—
( 82 )

Reagents

CN(C)c1ccncc1
4-DMAP

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherPreparation

Procedure

Preparation according to Preparation 22 using [7-(trifluoromethylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methanol (0.75 g, 2.5 mmol), toluenesulfonyl chloride (0.72 g, 3.8 mmol), TEA (0.42 ml, 3 mmol) and 4-DMAP (0.37 g, 3.0 mmol) in DCM (40 ml), stirred for 18 h. Yield 0.28 g. MS m/z (rel. intensity, 70 eV) 452 (M+, bp), 383 (41), 280 (82), 211 (80), 91 (84).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08524766B2uspto-grants-2013_09