Aluminium lithium hydride → (S)-(1-benzylpiperidin-2-yl)methanol

HRID 1006329Notes

Reaction equation

HRID 1006329 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][N:12]1[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O>O1CCCC1>[CH2:17]([N:12]1[CH2:13][CH2:14][CH2:15][CH2:16][C@H:11]1[CH2:9][OH:8])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69819234(2S)-1-benzylpiperidine-2-carboxylic acid methyl ester

Product 1

HCID 7021240(S)-(1-benzylpiperidin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride was added to an ice-cooled solution of (2S)-1-benzylpiperidine-2-carboxylic acid methyl ester (178 mg) in tetrahydrofuran (2.7 ml) under nitrogen atmosphere. The mixture was stirred for 2 hours below 5° C. The reaction was quenched by a sequential addition of water (0.12 ml), 15% aqueous sodium hydroxide (0.12 ml) and water (0.36 ml) successively, and the whole was stirred at room temperature for 1 hour. The insoluble materials were removed by filtration. The filtrate was dried over sodium sulfate and evaporated under reduced pressure to give (2S)-1-benzyl-2-(hydroxymethyl)piperidine as a colorless oil.

Workup

  1. customThe reaction was quenched by a sequential addition of water (0.12 ml), 15% aqueous sodium hydroxide (0.12 ml) and water (0.36 ml) successively
  2. stirringthe whole was stirred at room temperature for 1 hour
  3. customThe insoluble materials were removed by filtration
  4. dry with materialThe filtrate was dried over sodium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-72cc4f731e844f8f8abce74877dbf317
Source dataset
uspto-grants-2004_09
Patent number
US06787543B2

Reaction notes

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