Dichloromethane → (2R)-8-Fluoro-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl 4-methylbenzenesulfonate

HRID 39019

Reaction equation

HRID 39019 reaction equation
[F:1][C:2]1[C:7]2[O:8][C@@H:9]([CH2:12][OH:13])[CH2:10][O:11][C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:14]1(C)[C:15]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=1.[CH2:25](Cl)Cl>CN(C1C=CN=CC=1)C>[CH3:25][C:18]1[CH:19]=[CH:14][C:15]([S:20]([O:13][CH2:12][C@@H:9]2[O:8][C:7]3[C:2]([F:1])=[CH:3][CH:4]=[CH:5][C:6]=3[O:11][CH2:10]2)(=[O:21])=[O:22])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 8623o-Toluenesulfonyl chlorideHCID 54461939[(2S)-8-Fluoro-2,3-dihydro-1,4-benzodioxin-2-YL]methanol

Product 1

HCID 10759436(2R)-8-Fluoro-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Preparation according to Preparation 22 using [(2S)-8-fluoro-2,3-dihydro-1,4-benzodioxin-2-yl]methanol (7.05 g, 38.0 mmol), toluenesulfonyl chloride (10.9 g, 57 mmol), TEA (8.0 ml, 57 mmol) and 4-DMAP (4.7 g, 38.0 mmol) in DCM (75 ml), stirred for 1.5 h. Flash column chromatography yielded 11.9 g of the title compound. MS m/z (rel. intensity, 70 eV) 184 (90), 153 (43), 139 (29), 128 (bp), 57 (25).

Workup

  1. customPreparation

Sources & evidence

ORD record
ord-dc7db1bed65a49a697f7dc2bacc6624c
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Linked notes

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