4-Toluenesulfonyl chloride → [(2R)-2-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxy-ethyl] 4-methylbenzenesulfonate

HRID 60695Notes

Reaction equation

HRID 60695 reaction equation
[CH3:1][C:2]1([CH3:14])[O:6][C@H:5]2[O:7][C@H:8]([C@H:10]([OH:13])[CH2:11][OH:12])[CH2:9][C@H:4]2[O:3]1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>N1C=CC=CC=1>[CH3:25][C:15]1[CH:20]=[CH:19][C:18]([S:21]([O:12][CH2:11][C@H:10]([C@H:8]2[O:7][C@@H:5]3[O:6][C:2]([CH3:14])([CH3:1])[O:3][C@@H:4]3[CH2:9]2)[OH:13])(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 11084935(R)-1-((3AR,5S,6AR)-2,2-Dimethyltetrahydrofuro[2,3-D][1,3]dioxol-5-YL)ethane-1,2-diol

Product 1

HCID 15473566[(2R)-2-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxy-ethyl] 4-methylbenzenesulfonateYield 74%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (1R)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol (100 g, 490 mmol) in dry pyridine (1000 mL) was added p-toluenesulfonyl chloride (139 g, 735 mmol) at 0° C. After being stirred at room temperature for 12 hours, the resulted solution was quenched by water (100 mL) and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 1:10 to 1:3 EtOAc in petroleum ether) to afford 130 g of [(2R)-2-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxy-ethyl] 4-methylbenzenesulfonate (compound 6a) as a slight yellow oil.

Workup

  1. customthe resulted solution was quenched by water (100 mL)
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (eluting with 1:10 to 1:3 EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-6f26cc8ea12e4ece879f4c629c42d544
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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