(R)-3-Pyrrolidinol → 3-(4-Ethylphenyl)-5-{3-[(3R)-3-hydroxypyrrolidin-1-yl]-1,2,4-oxadiazol-5-yl}piperidin-1-yl(4-hydroxypiperidin-1-yl)methanone

HRID 661279Notes

Reaction equation

HRID 661279 reaction equation
Cl[C:2]1[N:6]=[C:5]([CH:7]2[CH2:12][CH:11]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=3)[CH2:10][N:9]([C:21]([N:23]3[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25][CH2:24]3)=[O:22])[CH2:8]2)[O:4][N:3]=1.[NH:30]1[CH2:34][CH2:33][C@@H:32]([OH:35])[CH2:31]1>C(O)C>[CH2:19]([C:16]1[CH:17]=[CH:18][C:13]([CH:11]2[CH2:12][CH:7]([C:5]3[O:4][N:3]=[C:2]([N:30]4[CH2:34][CH2:33][C@@H:32]([OH:35])[CH2:31]4)[N:6]=3)[CH2:8][N:9]([C:21]([N:23]3[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25][CH2:24]3)=[O:22])[CH2:10]2)=[CH:14][CH:15]=1)[CH3:20]

Participants

4

Reactant 2

HCID 2759337(R)-3-PyrrolidinolHCID 58116548[3-(3-Chloro-1,2,4-oxadiazol-5-yl)-5-(4-ethylphenyl)piperidin-1-yl](4-hydroxypiperidin-1-yl)-methanone

Product 1

HCID 498195603-(4-Ethylphenyl)-5-{3-[(3R)-3-hydroxypyrrolidin-1-yl]-1,2,4-oxadiazol-5-yl}piperidin-1-yl(4-hydroxypiperidin-1-yl)methanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 80.0 mg (0.191 mmol) of the oxadiazole from Example 25A in 1.20 ml of ethanol were added 333 mg (3.82 mmol) of (3R)-pyrrolidin-3-ol, and then the reaction mixture was stirred in the microwave at 80 for 2 h. The solvent was removed under reduced pressure, dichloromethane was added and the mixture was washed with water. The organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. Yield: 64.8 mg (70% of theory)

Workup

  1. customThe solvent was removed under reduced pressure, dichloromethane
  2. additionwas added
  3. washthe mixture was washed with water
  4. dry with materialThe organic phase was dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f67e7a1d41824ce2bc7e6d25aaa16bd7
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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