4-Toluenesulfonyl chloride → HCID 18665739, compound

HRID 365459Notes

Reaction equation

HRID 365459 reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([CH2:15][OH:16])[CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:23](Cl)([C:26]1[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=1)(=[O:25])=[O:24]>N1C=CC=CC=1>[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([CH2:15][O:16][S:23]([C:26]3[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH2:10]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 18665735HCID 18665735, compound

Product 1

HCID 18665739HCID 18665739, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-(2,2-Diphenylethyl)-3(S)-hydroxymethyl-piperidine (1.01 g, 3.41 mmol) was dissolved in dry pyridine (25 mL) and tosyl chloride (0.684 g, 3.58 mmol) was added to the solution After stirring at ambient temperature for 18 hr, the solution was concentrated, the residue taken up in EtOAc, washed with sat. NaHCO3 solution, H2O, brine, and dried (MgSO4). Filtration and concentration gave the title compound without further purification.

Workup

  1. concentrationthe solution was concentrated
  2. washwashed with sat. NaHCO3 solution, H2O, brine
  3. dry with materialdried (MgSO4)
  4. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-c5ad3ba1fe8f430fade08c79f4917f14
Source dataset
uspto-grants-2000_10
Patent number
US06127366

Reaction notes

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