4-Toluenesulfonyl chloride → HCID 68454482, compound

HRID 2246934Notes

Reaction equation

HRID 2246934 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][C@@H:11]([CH2:15][OH:16])[NH:12][CH2:13][CH:14]=2)=[CH:5][CH:4]=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>C(OCC)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][C@@H:11]([CH2:15][OH:16])[N:12]([S:23]([C:20]3[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=3)(=[O:25])=[O:24])[CH2:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 68443118(2S)-1,2,3,6-Tetrahydro-4-(4-methoxyphenyl)-2-pyridinemethanol

Product 1

HCID 68454482HCID 68454482, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Procedure

To a solution of 72.0 g of [(S)-4-(4-methoxy-phenyl)-1,2,3,6-tetrahydro-pyridin-2-yl]-methanol in 1.5 l of ethyl acetate and 1.5 l of 2N aqueous sodium carbonate are added 57.7 g of p-toluenesulfonyl chloride at 0° C. The reaction mixture is stirred overnight, extracted with ethyl acetate and the combined organic phases are dried over sodium sulfate and concentrated under reduced pressure. The crude product is used for the next step without any further purification. Rf=0.1 (EtOAc-heptane 1:1); Rt=4.20.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe combined organic phases are dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product is used for the next step without any further purification

Sources & evidence

ORD record
ord-397d8d5939344634867ff62c5132d217
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

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