1-{4-[5-(2-Fluorobiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]benzyl}-piperidine-4,4-dicarboxylic acid benzyl ester (2,2-dimethyl-propanoyl-oxymethyl) ester → 1-{4-[5-(2-Fluorobiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]benzyl}-piperidine-4,4-dicarboxylic acid (2,2-dimethyl-propanoyloxymethyl)ester

HRID 2407488Notes

Reaction equation

HRID 2407488 reaction equation
[CH3:1][C:2]([CH3:52])([CH3:51])[C:3]([O:5][CH2:6][O:7][C:8]([C:10]1([C:41]([O:43]CC2C=CC=CC=2)=[O:42])[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[N:27]=[C:26]([C:28]4[CH:33]=[CH:32][C:31]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)=[C:30]([F:40])[CH:29]=4)[O:25][N:24]=3)=[CH:19][CH:18]=2)[CH2:12][CH2:11]1)=[O:9])=[O:4]>C(O)C.C(OCC)(=O)C.[Pd]>[CH3:1][C:2]([CH3:52])([CH3:51])[C:3]([O:5][CH2:6][O:7][C:8]([C:10]1([C:41]([OH:43])=[O:42])[CH2:11][CH2:12][N:13]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[N:27]=[C:26]([C:28]4[CH:33]=[CH:32][C:31]([C:34]5[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=5)=[C:30]([F:40])[CH:29]=4)[O:25][N:24]=3)=[CH:21][CH:22]=2)[CH2:14][CH2:15]1)=[O:9])=[O:4]

Participants

5

Reactant 1

HCID 595094441-{4-[5-(2-Fluorobiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]benzyl}-piperidine-4,4-dicarboxylic acid benzyl ester (2,2-dimethyl-propanoyl-oxymethyl) ester

Product 1

HCID 595094451-{4-[5-(2-Fluorobiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]benzyl}-piperidine-4,4-dicarboxylic acid (2,2-dimethyl-propanoyloxymethyl)ester

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-{4-[5-(2-fluorobiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]benzyl}-piperidine-4,4-dicarboxylic acid benzyl ester (2,2-dimethyl-propanoyl-oxymethyl) ester (0.37 g, 0.00052 mol) in a mixture of ethanol and ethyl acetate (20 mL, 1:1) is added 5% Pd/C (0.133 g). The reaction mixture is stirred at room temperature and hydrogen gas is bubbled through it. This process is continued for 2.5 hours. The reaction mixture is filtered through a celite bed, washed with tetrahydrofuran (2×30 mL) and the filtrate is concentrated under reduced pressure to give a solid mass which is purified by column chromatography (silica gel 230-400 mesh, methanol:dichloromethane 15:85) to give 1-{4-[5-(2-fluorobiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]benzyl}-piperidine-4,4-dicarboxylic acid (2,2-dimethyl-propanoyloxymethyl)ester (e.g. 39).

Workup

  1. customhydrogen gas is bubbled through it
  2. filtrationThe reaction mixture is filtered through a celite bed
  3. washwashed with tetrahydrofuran (2×30 mL)
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customto give a solid mass which
  6. customis purified by column chromatography (silica gel 230-400 mesh, methanol:dichloromethane 15:85)

Sources & evidence

ORD record
ord-8ddf8425468744bb8863c95a17baaa36
Source dataset
uspto-grants-2014_08
Patent number
US08809539B2

Reaction notes

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