{4-[(R)-2-(3-Hydroxy-4-phenyl-butyl)-6-oxo-piperidin-1-yl]-butoxy}-acetonitrile → (R)-1-[4-(2-Amino-ethoxy)-butyl]-6-(3-hydroxy-4-phenyl-butyl)-piperidin-2-one

HRID 2052979Notes

Reaction equation

HRID 2052979 reaction equation
[OH:1][CH:2]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:3][CH2:4][C@H:5]1[CH2:10][CH2:9][CH2:8][C:7](=[O:11])[N:6]1[CH2:12][CH2:13][CH2:14][CH2:15][O:16][CH2:17][C:18]#[N:19].[H][H]>[Ni].CO>[NH2:19][CH2:18][CH2:17][O:16][CH2:15][CH2:14][CH2:13][CH2:12][N:6]1[C@@H:5]([CH2:4][CH2:3][CH:2]([OH:1])[CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:10][CH2:9][CH2:8][C:7]1=[O:11]

Participants

5

Reactant 2

HCID 69021316{4-[(R)-2-(3-Hydroxy-4-phenyl-butyl)-6-oxo-piperidin-1-yl]-butoxy}-acetonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 69021162(R)-1-[4-(2-Amino-ethoxy)-butyl]-6-(3-hydroxy-4-phenyl-butyl)-piperidin-2-oneYield 65.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Raney nickel (5 mg) was added to a solution of {4-[(R)-2-(3-hydroxy-4-phenyl-butyl)-6-oxo-piperidin-1-yl]-butoxy}-acetonitrile (10.5 mg, 0.029 mmol) in MeOH (1.5 mL). A hydrogen atmosphere was established by evacuating and refilling with hydrogen (3×) and the reaction mixture was stirred under a balloon of hydrogen for 19 h. The reaction mixture was filtered through celite, washing with MeOH, and the filtrate was concentrated in vacuo to afford 6.9 mg (65%) of the title compound.

Workup

  1. customby evacuating
  2. filtrationThe reaction mixture was filtered through celite
  3. washwashing with MeOH
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-030cda6a248f43318c22729aba006e89
Source dataset
uspto-grants-2008_02
Patent number
US07326716B2

Reaction notes

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