HCID 19097385, compound → HCID 19738112, compound

HRID 2255422Notes

Reaction equation

HRID 2255422 reaction equation
[CH3:1][N:2]1[CH:7]([CH3:8])[C:6]2([CH3:12])[CH:9]([CH3:11])[CH2:10][CH:3]1[CH:4]([C:13](OCC)=[O:14])[CH2:5]2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH3:1][N:2]1[CH:7]([CH3:8])[C:6]2([CH3:12])[CH:9]([CH3:11])[CH2:10][CH:3]1[CH:4]([CH2:13][OH:14])[CH2:5]2

Participants

4

Reactant 2

HCID 19097385HCID 19097385, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19738112HCID 19738112, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of ethyl 2,3,4,8-tetramethyl-2-azabicyclo-[2.2.2]octane-6-carboxylate (18.3 g, 76.5 mmol) in ether (200 mL) was added to a slurry of lithium aluminum hydride (5.8 g, 153 mmol) in ether (60 mL). The mixture was stirred for 1 hour, cooled to 0° C. and quenched by the sequential addition of water (5.8 mL), 15% NaOH (5.8 mL), and water (17.4 mL). The aluminum salts were removed by filtration and the filtrate was concentrated in vacuo to afford 14.8 g (98%) of 2,3,4,8-tetramethyl-2-azabicyclo[2.2.2]octane-6-methanol as a colorless oil. The product was dissolved in ether and treated with 4.9N ethereal.HCl to afford 9.1 g of the hydrochloride salt as a white solid, m.p. 158°-159° C.

Workup

  1. customquenched by the sequential addition of water (5.8 mL), 15% NaOH (5.8 mL), and water (17.4 mL)
  2. customThe aluminum salts were removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a02c43409e144e15a9a3ba50158c967c
Source dataset
uspto-grants-1993_08
Patent number
US05240935

Reaction notes

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