Water → 2-[1-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-methylpiperidin-3-yl]propan-2-ol

HRID 453781Notes

Reaction equation

HRID 453781 reaction equation
C(O[C:4]([C:6]1(C)[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH:13]2[O:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)[CH2:7]1)=O)C.[CH3:24][Mg]Cl.O.[CH2:28]1[CH2:32][O:31]CC1>>[O:18]1[C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[O:15][CH2:14][CH:13]1[CH2:12][N:8]1[CH2:9][CH2:10][CH2:11][C:6]([C:32]([OH:31])([CH3:28])[CH3:24])([CH3:4])[CH2:7]1

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 251755001-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-methylpiperidine-3-carboxylic acid ethyl esterHCID 178418332HCID 178418332, compound

Product 1

HCID 251756642-[1-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-methylpiperidin-3-yl]propan-2-ol

Procedure

To a solution of 1-(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-methylpiperidine-3-carboxylic acid ethyl ester (1.13 g, 3.53 mmol) in dry THF (50 ml) under nitrogen at 0° C. a solution of methyl magnesium chloride in THF (3.53 ml, 3.0 M) was added dropwise. The resulting solution was refluxed for 2.5 h. Water was then slowly added under cooling and the product was extracted with DCM and purified by column chromatography (DCM/MeOH, 95:5) to give the title compound.

Workup

  1. temperatureThe resulting solution was refluxed for 2.5 h
  2. temperatureunder cooling
  3. extractionthe product was extracted with DCM
  4. custompurified by column chromatography (DCM/MeOH, 95:5)

Sources & evidence

ORD record
ord-449c7a81091147c591de347385a3faa8
Source dataset
uspto-grants-2013_07
Patent number
US08492549B2

Reaction notes

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