Aluminium lithium hydride → {4-[(R)-2-(3-Hydroxy-4-phenyl-butyl)-6-oxo-piperidin-1-yl]-butoxy}-acetonitrile

HRID 2052978Notes

Reaction equation

HRID 2052978 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]=[C:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([CH2:14][CH2:15][C:16](=[O:24])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:9]1[CH2:25][CH2:26][CH2:27][CH2:28][O:29][CH2:30][C:31]#[N:32]>C1COCC1>[OH:24][CH:16]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:15][CH2:14][C@H:10]1[CH2:11][CH2:12][CH2:13][C:8](=[O:7])[N:9]1[CH2:25][CH2:26][CH2:27][CH2:28][O:29][CH2:30][C:31]#[N:32]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69022837{4-[(R)-2-Oxo-6-(3-oxo-4-phenyl-butyl)-piperidin-1-yl]-butoxy}-acetonitrile

Product 1

HCID 69021316{4-[(R)-2-(3-Hydroxy-4-phenyl-butyl)-6-oxo-piperidin-1-yl]-butoxy}-acetonitrileYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (1.0 M in THF, 0.02 mL, 0.02 mmol) was added to a solution of {4-[(R)-2-oxo-6-(3-oxo-4-phenyl-butyl)-piperidin-1-yl]-butoxy}-acetonitrile (15.7 mg, 0.044 mmol) in THF (0.75 mL) at 0° C. After 2 h at 0° C. the reaction was quenched with saturated aqueous NH4Cl (5 mL) and extracted with (3×5 mL). The combined organic phase was dried (Na2SO4), filtered and concentrated in vacuo to afford 12.3 mg (78%) of the title compound.

Workup

  1. customAfter 2 h at 0° C. the reaction was quenched with saturated aqueous NH4Cl (5 mL)
  2. extractionextracted with (3×5 mL)
  3. dry with materialThe combined organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0014af77d1e246a69f3a6ffeb6ca143d
Source dataset
uspto-grants-2008_02
Patent number
US07326716B2

Reaction notes

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