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

HRID 2407276Notes

Reaction equation

HRID 2407276 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-a7d0500b6a184af9a1627b168b46051c
Source dataset
uspto-grants-2014_08
Patent number
US08809536B2

Reaction notes

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