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

HRID 547183

Reaction equation

HRID 547183 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 aluminum 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-358144f660614c7e80a93663495202a3
Source dataset
uspto-grants-2011_05
Patent number
USRE042353E1

Linked notes

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