Water → 3-(5-Hydroxy-2-naphthylsulfonyl)-3-azabicyclo[3.2.2]nonane

HRID 725783Notes

Reaction equation

HRID 725783 reaction equation
C([O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9]([S:15]([N:18]1[CH2:24][CH:23]3[CH2:25][CH2:26][CH:20]([CH2:21][CH2:22]3)[CH2:19]1)(=[O:17])=[O:16])=[CH:10]2)(=O)C.O.C(=O)(O)[O-].[Na+]>C1COCC1>[OH:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9]([S:15]([N:18]1[CH2:24][CH:23]3[CH2:25][CH2:26][CH:20]([CH2:21][CH2:22]3)[CH2:19]1)(=[O:17])=[O:16])=[CH:10]2

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 197087183-(5-Acetoxy-2-naphthylsulfonyl)-3-azabicyclo[3.2.2]nonane

Product 1

HCID 197087333-(5-Hydroxy-2-naphthylsulfonyl)-3-azabicyclo[3.2.2]nonane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared from 3-(5-Acetoxy-2-naphthylsulfonyl)-3-azabicyclo[3.2.2]nonane, by dissolving the acetoxy compound in 3 ml THF and then adding 2 ml water and 2 ml saturated sodium bicarbonate solution. After stirring overnight, the solvent was evaporated and the product extracted with chloroform. After drying over magnesium sulfate, the solvent was evaporated to give an orange oil. This was purified by chromatotron using 3/1 hexane/ethyl acetate which gave a yellow solid (32 mg, 48% yield): 1H NMR (CDCl3): 8.33 (d, J=8.8, 1 H, H3), 8.25 (d, J=1.6, 1 H, H1), 7.70 (d, J=8.8, 1 H, H4), 7.49 (d, J=8.3, 1 H, H6), 7.40 (t, J=7.8, 1 H, H7), 7.02 (d, J=7.4, 1 H, H8), 6.68 (br s, 1 H, OH), 3.30 (d, J=4.2, 4 H, N(CH2R)2), 2.08 (s, 2 H, N(CH2CHR)2),1.72-1.58 (in, 8 H, alkyl H's).

Workup

  1. customthe solvent was evaporated
  2. extractionthe product extracted with chloroform
  3. dry with materialAfter drying over magnesium sulfate
  4. customthe solvent was evaporated
  5. customto give an orange oil
  6. customThis was purified by chromatotron

Sources & evidence

ORD record
ord-c878c0d7b9da458e825989bdd2fe262e
Source dataset
uspto-grants-1998_01
Patent number
US05707985

Reaction notes

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