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

HRID 2407272Notes

Reaction equation

HRID 2407272 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10]([C:12]1([CH3:29])[CH2:17][CH2:16][CH2:15][N:14]([CH2:18][CH:19]2[O:24][C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[O:21][CH2:20]2)[CH2:13]1)=O)C.O>C1COCC1>[O:24]1[C:23]2[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=2[O:21][CH2:20][CH:19]1[CH2:18][N:14]1[CH2:15][CH2:16][CH2:17][C:12]([CH2:10][OH:9])([CH3:29])[CH2:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 251755001-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-methylpiperidine-3-carboxylic acid ethyl ester

Product 1

HCID 66726912[1-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-methylpiperidin-3-yl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LiAlH4 (0.59 g, 15.54 mmol) in dry THF (45 ml), was added 1-(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-methylpiperidine-3-carboxylic acid ethyl ester (1.0 g, 3.13 mmol) in dry THF (5 ml). The reaction mixture was refluxed for 1 h. Water was slowly added and the reaction mixture was extracted with EtOAc (3×20 ml). The combined organic phases were dried over Na2SO4, filtered and the filtrate was evaporated to give the desired product which, was purified by column chromatography (EtOAc/heptane, 50:50).

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. extractionthe reaction mixture was extracted with EtOAc (3×20 ml)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-2a61b39e2d9c46dd89d37f3648975b40
Source dataset
uspto-grants-2014_08
Patent number
US08809536B2

Reaction notes

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