HCID 9815620, compound → 3-(4-Fluorophenyl)-8-azabicyclo[3.2.1]octane

HRID 378554Notes

Reaction equation

HRID 378554 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:14][CH:13]3[NH:15][CH:10]([CH2:11][CH2:12]3)[CH:9]=2)=[CH:4][CH:3]=1.[H][H]>C(O)(=O)C.[Pt]=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:14][CH:13]3[NH:15][CH:10]([CH2:11][CH2:12]3)[CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 9815620HCID 9815620, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 220122293-(4-Fluorophenyl)-8-azabicyclo[3.2.1]octaneYield 89.1%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 3-(4-fluorophenyl)-8-azabicyclo[3,2,1]oct-2-ene (10 g) was dissolved in glacial acetic acid (150 ml). Platinum oxide (0.5 g) was added followed by treatment with hydrogen gas at 3 atm of pressure in a conventional Parr apparatus. Filtration and removal of solvent in vacuo left a viscous oil. Water was added and the mixture made alkaline (pH>9) with aqeous NaOH. Extraction with ethyl acetate, drying of the organic phase over magnesium sulfate and removal of solvent in vacuo gave 3-(4-fluorophenyl)-8-azabicyclo[3,2,1]-octane (9 g) as an oil. The title compound 24 was obtained from 3-(4-fluorophenyl)-8-azabicyclo[3,2,1]octane and 4-(1,2-benzisoxazol-3-yl)-1-butyl methanesulfonate (prepared as described in EXAMPLE 19) by the method described in EXAMPLE 2. The oxalate salt crystallized from acetone by addition of oxalic acid. Yield. 1.1 g, mp: 169-70° C.

Workup

  1. filtrationFiltration and removal of solvent in vacuo
  2. waitleft a viscous oil
  3. additionWater was added
  4. extractionExtraction with ethyl acetate
  5. dry with materialdrying of the organic phase over magnesium sulfate and removal of solvent in vacuo

Sources & evidence

ORD record
ord-f01d3506dd424781bcec057b08e32b58
Source dataset
uspto-grants-2000_02
Patent number
US06031099

Reaction notes

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