Diethyl Ether → HCID 18457668, compound

HRID 1272516Notes

Reaction equation

HRID 1272516 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:15][CH2:14][CH2:13][CH:12]2[CH:23]=[O:24])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:25][Mg]Br.CCOCC.[Cl-].[NH4+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:15][CH2:14][CH2:13][CH:12]2[CH:23]([OH:24])[CH3:25])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 184576701-(4-Chloro-benzenesulfonyl)-6-phenyl-piperidine-2-carbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 18457668HCID 18457668, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of step 1 (232 mg; 0.64 mmol) in THF (6 mL) at 0° C. was added methyl magnesium bromide solution 3 N in Et2O (0.27 mL; 0.83 mmol) and the reaction was allowed to warm to room temperature for 1 h. The mixture was poured into saturated ammonium chloride, extracted with DCM, and dried over Na2SO4. After concentration of the solvents, the residue was purified by chromatography over silica gel (eluting Hexanes/EtOAc 8:2) to give 240 mg (100%) of 1-[1-(4-chloro-benzenesulfonyl)-6-phenyl-piperidin-2-yl]-ethanol as a ca 4.5:1 mixture of diastereoisomers.

Workup

  1. extractionextracted with DCM
  2. dry with materialdried over Na2SO4
  3. customAfter concentration of the solvents, the residue was purified by chromatography over silica gel (eluting Hexanes/EtOAc 8:2)

Sources & evidence

ORD record
ord-f648c4e641764845a0c767906493557d
Source dataset
uspto-grants-2007_04
Patent number
US07208602B2

Reaction notes

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