HCID 19703131, compound → HCID 19703156, compound

HRID 861432Notes

Reaction equation

HRID 861432 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]3([OH:23])[CH:20]4[CH2:21][CH2:22][N:17]([CH2:18][CH2:19]4)[CH2:16]3)=[CH:9][CH:8]=2)[N:3]=1>C(O)C.[Pd]>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][C:15]3([OH:23])[CH:20]4[CH2:21][CH2:22][N:17]([CH2:18][CH2:19]4)[CH2:16]3)=[CH:11][CH:12]=2)[N:3]=1

Participants

4

Reactant 1

HCID 19703131HCID 19703131, compound

Product 1

HCID 19703156HCID 19703156, compoundYield 24.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-[2-(4-(5-methyl-1,2,4-oxadiazole-3-yl)phenyl)ethynyl]-3-hydroxyquinuclidine (0.61 g) and 5% Pd on carbon (60 mg) in ethanol (100 ml) was hydrogenated at atmospheric pressure for 4 hours. The mixture was filtered and the filtrate was evaporated. The residue was purified by flash chromatography on silica gel eluting with 10% methanol in dichloromethane containing 1% ammonia (density, 0.88 g/cm3), to give 3-[2-(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)ethyl]-3-hydroxyquinuclidine (0.15 g) as a solid, m.p. 165°-167° C.; NMR: 1.2-2.1(7H,m), 2.9-2.65(8H,m), 2.65(3H,s), 4.5(1H,s), 7.4(2H,d) and 7.9(2H,d); m/z 314 (M+H).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. customThe residue was purified by flash chromatography on silica gel eluting with 10% methanol in dichloromethane containing 1% ammonia (density, 0.88 g/cm3)

Sources & evidence

ORD record
ord-909214c9fa3c40809bfe4c56d1150edb
Source dataset
uspto-grants-1998_02
Patent number
US05714496

Reaction notes

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