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

HRID 454002

Reaction equation

HRID 454002 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([C:8](OCC)=[O:9])[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC.C1COCC1>[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([CH2:8][OH:9])[CH2:3]1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 736036ethyl (3R)-1-methylpiperidine-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 920113(R)-(1-methylpiperidin-3-yl)methanolYield 94.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A solution of (R)-ethyl 1-methylpiperidine-3-carboxylate (5.69 g, 33 mmol) in ether (20 ml) was added dropwise to a stirred solution of lithium aluminium hydride (36.6 ml of a 1M solution in THF, 36.6 mmol) in ether (85 ml) cooled to maintain a reaction temperature of 20° C. The mixture was stirred for 1.5 hours at ambient temperature and then water (1.4 ml), 15% aqueous sodium hydroxide solution (1.4 ml) and then water (4.3 ml) were added. The insolubles were removed by filtration and the volatiles removed from the filtrate by evaporation to give (R)-(1-methylpiperidin-3-yl)methanol (4.02 g, 94%) as a colourless oil.

Workup

  1. temperaturecooled
  2. customThe insolubles were removed by filtration
  3. customthe volatiles removed from the filtrate by evaporation

Sources & evidence

ORD record
ord-1e40f4b3c64b468296342a4fc7788663
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Linked notes

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