p-Toluenesulfonic acid monohydrate → (2R,3R)-1-Chloro-2-(2,4-difluorophenyl)butane-2,3-diol

HRID 731017Notes

Reaction equation

HRID 731017 reaction equation
[Cl:1][CH2:2][C@:3]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[F:21])([OH:13])[C@H:4]([O:6]C1CCCCO1)[CH3:5].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[Cl:1][CH2:2][C@:3]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[F:21])([OH:13])[C@H:4]([OH:6])[CH3:5]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 11602194(2R,3R)-1-chloro-2-(2,4-difluorophenyl)-3-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)butan-2-ol

Product 1

HCID 67175587(2R,3R)-1-Chloro-2-(2,4-difluorophenyl)butane-2,3-diolYield 107.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixed solution of 0.15 g (0.47 mmol) of (2R,3R)-1-chloro-2-(2,4-difluorophenyl)-3-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)butan-2-ol, 5 mL of methanol, and 0.02 g of p-toluenesulfonic acid monohydrate was stirred at room temperature for 30 minutes. Concentration was performed under reduced pressure to obtain a crude product. The resulting product was purified by column on silica gel to obtain 0.12 g of the title compound (yield: 97%).

Workup

  1. concentrationConcentration
  2. customto obtain a crude product
  3. customThe resulting product was purified by column on silica gel

Sources & evidence

ORD record
ord-a46471aa06364ff59d00bf45c253c3e8
Source dataset
uspto-grants-2009_09
Patent number
US07582781B2

Reaction notes

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