4-Toluenesulfonyl chloride → [(2S)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate

HRID 38991

Reaction equation

HRID 38991 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH2:12][C@@H:11]([CH2:14][OH:15])[O:10][C:9]=2[CH:16]=1)(=[O:4])=[O:3].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([O:15][CH2:14][C@H:11]2[O:10][C:9]3[CH:16]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=[CH:7][C:8]=3[O:13][CH2:12]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 66878426[(2R)-7-(Methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methanol

Product 1

HCID 86652934[(2S)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonateYield 87.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Preparation according to Preparation 5 using [[(2R)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methanol (2.1 g, 8.6 mmol), p-toluenesulfonyl chloride (2.5 g, 12.8 mmol), TEA (1.8 ml, 12.8 mmol) and 4-DMAP (1.0 g, 8.6 mmol) and DCM (dry, 20 ml). DCM (50 ml) was added and the solution was washed with HCl (100 ml, 1 N), water (100 ml) and brine (100 ml) and was evaporated to dryness to give the title compound (3.0 g). MS m/z (rel. intensity, 70 eV) 398 (M+, 49), 226 (bp), 225 (24), 213 (30), 91 (68).

Workup

  1. customPreparation
  2. washthe solution was washed with HCl (100 ml, 1 N), water (100 ml) and brine (100 ml)
  3. customwas evaporated to dryness

Sources & evidence

ORD record
ord-3c5bcdcddd854d5cb69716ee1cb31f4f
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Linked notes

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