Aluminium lithium hydride → 951223-50-0

HRID 732937Notes

Reaction equation

HRID 732937 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16](=O)[NH:17][CH3:18])[CH2:10][CH2:9]1)=O)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:18][NH:17][CH2:16][CH2:15][CH2:14][CH:11]1[CH2:12][CH2:13][N:8]([CH3:6])[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68657765HCID 68657765, compound

Product 1

HCID 68657539951223-50-0Yield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 4-(2-methylcarbamoyl-ethyl)-piperidine-1-carboxylic acid tert-butyl ester (3.00 g, 11.1 mmol) in THF (100 mL) was added LiAlH4 pellets (1.69 g, 4.47 mmol). The mixture was stirred at 0° C. for 1 h, and then was heated at 70° C. for 4 h. The mixture was cooled to 0° C. and quenched sequentially (slowly) with water (1.7 mL), 10% NaOH (1.7 mL), and water (1.7 mL). The resulting slurry was filtered through diatomaceous earth and the filtrate was concentrated to yield 1.6 g (85%) of the product as a yellow oil. MS: mass calcd. for C10H22N2, 170.18; m/z found, 171.3 [M+H]+.

Workup

  1. temperaturewas heated at 70° C. for 4 h
  2. temperatureThe mixture was cooled to 0° C.
  3. customquenched sequentially (slowly) with water (1.7 mL), 10% NaOH (1.7 mL), and water (1.7 mL)
  4. filtrationThe resulting slurry was filtered through diatomaceous earth
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-336d7bd9dfea44d0acef651099ab6ac3
Source dataset
uspto-grants-2009_09
Patent number
US07589087B2

Reaction notes

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