HCID 67740377, compound → HCID 67850599, compound

HRID 580958Notes

Reaction equation

HRID 580958 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2([OH:22])[CH:19]3[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]3)[CH2:15]2)=[CH:8][CH:7]=1.[H][H]>C(O)C.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][C:14]2([OH:22])[CH:19]3[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]3)[CH2:15]2)=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 67740377HCID 67740377, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67850599HCID 67850599, compoundYield 38.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-[2-{4-(2-methoxyethoxy)phenyl}ethynyl]-quinuclidin-3-ol (1.8 g) in ethanol (200 ml) and a catalyst of 10% (v/v) palladium on carbon (100 mg) was stirred under an atmosphere of hydrogen until hydrogen uptake ceased. The palladium/carbon catalyst was removed by filtration and the filtrate was evaporated. The residue was crystallised from a 3:1 (v/v) mixture of cyclohexane ethylacetate to give 3-[2-{4-(2-methoxyethoxy)phenyl}ethyl]quinuclidin-3-ol (700 mg) as a solid, mpt 116-117° C. Microanalysis, found C,71.1; H,9.2; N,4.5%; C18H27NO3 requires: C,70.8; H,8.9; N,4.59%; NMR ([CD3 ]2SO): 1.15-1.35 (1H, m), 1.4-1.6 (1H, m), 1.65-1.78 (2H, m), 1.9-2.08 (1H, m), 2.45-2.8 (10H, m), 3.3 (3H, s), 3.6-3.68 (2H, m), 4.0-4.08 (2H, m), 4.3 (1H, br), 6.78-6.86 (2H, d), 7.05-7.13 (2H, d); m/z 306 (M+H).

Workup

  1. customThe palladium/carbon catalyst was removed by filtration
  2. customthe filtrate was evaporated
  3. customThe residue was crystallised from a 3:1 (v/v) mixture of cyclohexane ethylacetate

Sources & evidence

ORD record
ord-e7c198cb67894fb783274784cab4c370
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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