Aluminium lithium hydride → [1-Benzyl-4-(2-fluorobenzyl)piperidin-4-yl)methanol

HRID 270043Notes

Reaction equation

HRID 270043 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])([C:14](OCC)=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:14][OH:15])([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59833634Ethyl 1-benzyl-4-(2-fluorobenzyl)piperidine-4-carboxylate

Product 1

HCID 68961767[1-Benzyl-4-(2-fluorobenzyl)piperidin-4-yl)methanolYield 61.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A stirred solution of ethyl 1-benzyl-4-(2-fluorobenzyl)piperidine-4-carboxylate (1.85 g, 5.2 mmol) in diethyl ether was cooled on ice/sodium chloride. Lithium aluminium hydride (5.8 mL, 1.0 M in diethyl ether) was added drop wise. After stirring at room temperature for 2 hrs the mixture was re-cooled on ice, quenched with water/sodium hydroxide (10%) and stirred at room temperature for 1 hrs. The solids were filtered off, and the organic layer was dried over disodium sulphate, filtrated and concentrated. The crude material was purified on silica (dichloromethane/ethanol) to give 1.0 g (61%) the subtitle compound.

Workup

  1. temperaturewas re-cooled on ice
  2. customquenched with water/sodium hydroxide (10%)
  3. stirringstirred at room temperature for 1 hrs
  4. filtrationThe solids were filtered off
  5. dry with materialthe organic layer was dried over disodium sulphate
  6. filtrationfiltrated
  7. concentrationconcentrated
  8. customThe crude material was purified on silica (dichloromethane/ethanol)

Sources & evidence

ORD record
ord-18c3dc96c2444d1c8907860676f650a2
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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