HCID 66639453, compound → HCID 59799850, compound

HRID 1094457Notes

Reaction equation

HRID 1094457 reaction equation
[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C@H:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[F:19])[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(N(C(C)C)CC)(C)C.CS(C)=O>[CH2:20]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@H:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[F:19])[CH:10]=[O:11])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 1

HCID 66639453HCID 66639453, compound

Product 1

HCID 59799850HCID 59799850, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of (R)-2-dibenzylamino-3-(2-fluoro-phenyl)-propan-1-ol (1 g, 2.9 mmol) in 2 mL of diisopropyl-ethyl-amine at 10° C. is slowly added a solution of sulfur trioxide pyridine complex (1.4 g, 8.6 mmol) in 5 mL of DMSO. The reaction is allowed to stir at room temperature for 45 minutes after which time the reaction is quenched by addition of ice water. The product is extracted into ether and the combined organic phases are washed with water, 5% citric acid, and brine. The organic layer is dried over sodium sulfate, filtered, and concentrated under reduce pressure to give the title compound.

Workup

  1. customis quenched by addition of ice water
  2. extractionThe product is extracted into ether
  3. washthe combined organic phases are washed with water, 5% citric acid, and brine
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-19486c9e4c2041dab2c52a3f3ba7992f
Source dataset
uspto-grants-2012_03
Patent number
US08133907B2

Reaction notes

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