Tetrahydrofuran → Rel-[(3r,4s)-4-phenylpiperidin-3-yl]methanol

HRID 1691663Notes

Reaction equation

HRID 1691663 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.O=[C:13]1[NH:18][CH2:17][C@H:16]([C:19](OC)=[O:20])[C@@H:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:14]1.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[C:23]1([C@H:15]2[CH2:14][CH2:13][NH:18][CH2:17][C@@H:16]2[CH2:19][OH:20])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59178494HCID 59178494, compound

Product 1

HCID 59977995Rel-[(3r,4s)-4-phenylpiperidin-3-yl]methanolYield 84.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
75 °C

Procedure

To a suspension of 1.8 g of lithium aluminum hydride in 40 mL of toluene—40 mL of THF was added 6.3 g of methyl rel-(3R,4S)-6-oxo-4-phenylpiperidine-3-carboxylate at room temperature. The reaction mixture was stirred at 75° C. for 35 hours. After completion of the reaction, it was cooled to room temperature, and 1.0 mL of water, 1.0 mL of a 1 M aqueous sodium hydroxide solution, and 1.0 mL of water added thereto in this order, followed by stirring for 10 minutes. This mixture was dried over anhydrous sodium sulfate, the insolubles were removed by filtration, and the filtrate was then concentrated under reduced pressure to obtain a white solid of 4.37 g of rel-[(3R,4S)-4-phenylpiperidin-3-yl]methanol as a crude product. ESI+: 192

Workup

  1. customAfter completion of the reaction, it
  2. temperaturewas cooled to room temperature
  3. stirringby stirring for 10 minutes
  4. dry with materialThis mixture was dried over anhydrous sodium sulfate
  5. customthe insolubles were removed by filtration
  6. concentrationthe filtrate was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-aa926dd74e5040be9334fe8760707384
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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