Methanol → 4'-Phenylthiospiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine]

HRID 48524Notes

Reaction equation

HRID 48524 reaction equation
[H-].[Na+].Cl[C:4]1[CH:9]=[CH:8][N:7]=[C:6]2[O:10][C:11]3([CH:17]4[CH2:18][CH2:19][N:14]([CH2:15][CH2:16]4)[CH2:13]3)[CH2:12][C:5]=12.[C:20]1([SH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CO>O1CCOCC1.O>[C:20]1([S:26][C:4]2[CH:9]=[CH:8][N:7]=[C:6]3[O:10][C:11]4([CH:17]5[CH2:18][CH2:19][N:14]([CH2:15][CH2:16]5)[CH2:13]4)[CH2:12][C:5]=23)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 7969ThiophenolHCID 24758Sodium hydrideHCID 100377734'-chlorospiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine]

Product 1

HCID 104264294'-Phenylthiospiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine]Yield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Sodium hydride (151 mg, 3.77 mmol) was added to a solution of 97 mg (0.387 mmol) of 4′-chlorospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine], 0.40 mL (3.91 mmol) of thiophenol and 0.10 mL of methanol in 15 mL of dioxane, under a nitrogen atmosphere. The reaction was refluxed for 4 days, cooled to ambient temperature, diluted with 30 mL of water, and extracted with chloroform (3×30 mL). The combined organic extract was dried over anhydrous magnesium sulfate, concentrated in vacuo and the residue flash chromatographed on neutral silica gel using a 98:2 mixture of ammoniated chloroform/methanol to give 65 mg (52%) of the title compound as a colourless oil: electrospray MS (m/z, relative intensity) 325 ([MH]+).

Workup

  1. temperatureThe reaction was refluxed for 4 days
  2. extractionextracted with chloroform (3×30 mL)
  3. extractionThe combined organic extract
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customthe residue flash chromatographed on neutral silica gel using
  7. additiona 98:2 mixture of ammoniated chloroform/methanol

Sources & evidence

ORD record
ord-2ed609fb0b094899946b144ee0a37d43
Source dataset
uspto-grants-2004_03
Patent number
US06703502B2

Reaction notes

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