Tetrahydrofuran → 4-(4-Fluorophenyl)-3-piperidinemethanol

HRID 2084607Notes

Reaction equation

HRID 2084607 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]2[CH2:19][C:18](=O)[NH:17][CH2:16][C@H:15]2[CH2:21]CC(O)=O)=[CH:10][CH:9]=1.[O:26]1CCCC1>>[F:7][C:8]1[CH:9]=[CH:10][C:11]([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH:15]2[CH2:21][OH:26])=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 69829520trans-4-(4-Fluorophenyl)-3-carboxyethylpiperidin-6-one

Product 1

HCID 98156874-(4-Fluorophenyl)-3-piperidinemethanolYield 76%

Conditions

Temperature
25 °C

Procedure

Lithium aluminum hydride (1.0 molar solution in tetrahydrofuran, 0.75 ml, 0.75 mmol) was added gradually to a solution of trans-4-(4-fluorophenyl)-3-carboxyethylpiperidin-6-one (0.25g, 0.836 mmol) in tetrahydrofuran (3 ml) keeping the temperature below 25° C. The reaction mixture was stirred for 1 hour at 25° C., then quenched with 1 drop of water, followed by 2 drops 15% sodium hydroxide solution, and finally with 5 drops of water. Extraction with dichloromethane (35 ml) followed by evaporation of the dichloromethane phase gave 0.21 g of the title compound. Yield 76%.

Workup

  1. customthe temperature below 25° C
  2. customquenched with 1 drop of water
  3. extractionExtraction with dichloromethane (35 ml)
  4. customfollowed by evaporation of the dichloromethane phase

Sources & evidence

ORD record
ord-59f36b09cdea489d88b94d2acd13273b
Source dataset
uspto-grants-2004_04
Patent number
US06716985B2

Reaction notes

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