Potassium Carbonate → 1-[3-(4-Benzyloxy-phenyl)-isoxazol-5-ylmethyl]-piperidin-4-ol

HRID 72330Notes

Reaction equation

HRID 72330 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([CH2:20]OS(C)(=O)=O)[O:17][N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:26][CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.C(=O)([O-])[O-].[K+].[K+]>CCCC[N+](CCCC)(CCCC)CCCC.[I-].CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:19]=[C:18]([CH2:20][N:30]3[CH2:31][CH2:32][CH:27]([OH:26])[CH2:28][CH2:29]3)[O:17][N:16]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79341Piperidin-4-olHCID 59667381Methanesulfonic acid 3-(4-benzyloxy-phenyl)-isoxazol-5-ylmethyl ester

Product 1

HCID 468937801-[3-(4-Benzyloxy-phenyl)-isoxazol-5-ylmethyl]-piperidin-4-ol

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent2×

Procedure

Methanesulfonic acid-3-(4-benzyloxy-phenyl)-isoxazol-5-ylmethyl ester (150 mg, 0.42 mmol), 4-hydroxypiperidine (64 mg, 0.63 mmol), potassium carbonate (87 mg, 0.63 mmol), and TBAI (96 mg, 0.26 mmol) were placed in 10 ml of DMF and stirred at room temperature overnight. The completion of the reaction was confirmed by LC, and then a crude solid compound obtained from distillation of the DMF under reduced pressure was extracted with ethyl acetate and water. The ethyl acetate was distilled off under reduced pressure to obtain a white solid compound. The compound was recrystallized from methylene chloride:MeOH (9:1) to obtain 1-[3-(4-benzyloxy-phenyl)-isoxazol-5-ylmethyl]-piperidin-4-ol as a white solid compound.

Workup

  1. extractionwas extracted with ethyl acetate and water
  2. distillationThe ethyl acetate was distilled off under reduced pressure
  3. customto obtain a white solid compound
  4. customThe compound was recrystallized from methylene chloride:MeOH (9:1)

Sources & evidence

ORD record
ord-9e99c9c601a74a2eb500d37040d2a407
Source dataset
uspto-grants-2014_09
Patent number
US08828992B2

Reaction notes

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