Tetrahydrofuran → {(S)-1-[(S)-1-(2,3-Dihydrobenzo[1,4]dioxin-2-yl)methyl]-3-methylpiperidin-3-yl}methanol

HRID 453811Notes

Reaction equation

HRID 453811 reaction equation
C([O:3][C:4]([C@@:6]1([CH3:24])[CH2:11][CH2:10][CH2:9][N:8]([C:12]([C@@H:14]2[O:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[O:16][CH2:15]2)=O)[CH2:7]1)=O)C.C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O>[O:19]1[C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=2[O:16][CH2:15][C@@H:14]1[CH2:12][N:8]1[CH2:9][CH2:10][CH2:11][C@@:6]([CH2:4][OH:3])([CH3:24])[CH2:7]1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 66727067(S)-1-((R)-2,3-Dihydrobenzo[1,4]dioxine-2-carbonyl)-3-methylpiperidine-3-carboxylic acid ethyl ester

Product 1

HCID 25176123{(S)-1-[(S)-1-(2,3-Dihydrobenzo[1,4]dioxin-2-yl)methyl]-3-methylpiperidin-3-yl}methanolYield 95.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (S)-1-((R)-2,3-dihydrobenzo[1,4]dioxine-2-carbonyl)-3-methylpiperidine-3-carboxylic acid ethyl ester (27.7 g, 83.1 mmol) and THF (150 ml) was added to a cooled (0° C.) mixture of dry THF (150 ml) and LiAlH4 (10 g, 264 mmol). The reaction mixture was refluxed for 2 h, after which it was cooled to RT and water was added. The mixture was extracted twice with EtOAc and dried with Na2SO4. Solvent was evaporated to give 21.93 g of the title compound.

Workup

  1. additionwas added to
  2. temperaturea cooled
  3. temperatureThe reaction mixture was refluxed for 2 h
  4. extractionThe mixture was extracted twice with EtOAc
  5. dry with materialdried with Na2SO4
  6. customSolvent was evaporated

Sources & evidence

ORD record
ord-04096f1560e742f5944818d757ddb5fb
Source dataset
uspto-grants-2013_07
Patent number
US08492549B2

Reaction notes

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