Water → (R)-(1-methylpiperidin-3-yl)methanol

HRID 2262478Notes

Reaction equation

HRID 2262478 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][CH2:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15](OC(C)(C)C)=O)[CH2:10]1.[OH-].[Na+].O>C1COCC1>[CH3:15][N:11]1[CH2:12][CH2:13][CH2:14][C@@H:9]([CH2:8][OH:7])[CH2:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 1514447tert-butyl (3R)-3-(hydroxymethyl)piperidine-1-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 920113(R)-(1-methylpiperidin-3-yl)methanolYield 106.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 2M solution of LiAlH4 in THF (14.0 mL, 28.0 mmol) was added drop-wise to a solution of (R)-tert-butyl 3-(hydroxymethyl)piperidine-1-carboxylate (5.00 g, 23.2 mmol) in THF (30 mL) under argon at 0° C. The reaction mixture was allowed to warm to room temperature over 2 hours and stirred at room temperature for 17 hours. The reaction mixture was cooled to 0° C. and a 1M aq NaOH solution (4.0 mL) was added drop-wise. Water (2 mL) was added and the resulting mixture stirred at room temperature for 2 hours. The white solid was removed by filtration. The filtrate was concentrated in vacuo to give (R)-(1-methylpiperidin-3-yl)methanol (3.19 g, 106%) as a colourless oil which was used without further purification.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringthe resulting mixture stirred at room temperature for 2 hours
  3. customThe white solid was removed by filtration
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-bafbc63b03fa4375ba9e306f38155e82
Source dataset
uspto-grants-2010_12
Patent number
US07851471B2

Reaction notes

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