Aluminium lithium hydride → HCID 70202328, compound

HRID 1276511Notes

Reaction equation

HRID 1276511 reaction equation
[C:1]12([C:11]([N:13]3[CH2:17][CH:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:15]([CH2:24][N:25]4[CH2:30][CH2:29][CH:28]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[CH2:27][CH2:26]4)[CH2:14]3)=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:1]12([CH2:11][N:13]3[CH2:17][CH:16]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:15]([CH2:24][N:25]4[CH2:30][CH2:29][CH:28]([C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=5)[CH2:27][CH2:26]4)[CH2:14]3)[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 70198743HCID 70198743, compound

Product 1

HCID 70202328HCID 70202328, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(1-adamantanecarbonyl)-3-(RS)-((4-phenyl)piperidin-1-yl)methyl-4-(SR)-phenylpyrrolidine (10 mg, 0.021 mmol) in 2 mL of THF was added lithium aluminum hydride (2 mg, 0.042 mmol). The reaction was heated to reflux. After 2 hours the reaction was quenched with H2O (0.5 mL), 15% NaOH solution (0.5 mL), H2O (1.0 mL) and diluted with a saturated solution of Rochelle salts (50 mL) and CH2Cl2 (50 mL). After stirring for 1 hour the mixture was extracted with CH2Cl2 (3×50 mL). The combined organic extracts were washed with brine, dried (Na2SO4), and concentrated in vacuo to yield 9 mg of the title compound. Mass Spectrum (NH3 -CI): 469 (M+1).

Workup

  1. temperatureThe reaction was heated to reflux
  2. customAfter 2 hours the reaction was quenched with H2O (0.5 mL), 15% NaOH solution (0.5 mL), H2O (1.0 mL)
  3. additiondiluted with a saturated solution of Rochelle salts (50 mL) and CH2Cl2 (50 mL)
  4. extractionwas extracted with CH2Cl2 (3×50 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2fd16308edd84b96aa987fd0c121ec29
Source dataset
uspto-grants-2000_12
Patent number
US06166037

Reaction notes

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