Water → 3-Benzyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane

HRID 8573Notes

Reaction equation

HRID 8573 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:21][CH:20]2[O:22][CH:16]([CH2:17][N:18](S(C3C=CC=CC=3)(=O)=O)[CH2:19]2)[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[K+]>O1CCCC1>[CH2:7]([N:14]1[CH2:21][CH:20]2[O:22][CH:16]([CH2:17][NH:18][CH2:19]2)[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14797Potassium HydroxideHCID 160364063-Benzyl-7-(phenylsulfonyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonaneHCID 21226445Aluminium lithium hydride

Product 1

HCID 160364073-Benzyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

10.00 g (0.25 mol) of lithium aluminum hydride are introduced into 300 ml of absolute tetrahydrofuran and heated to reflux, and 18.00 g (50 mmol) of 7-benzyl-3-phenylsulfonyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane, dissolved in 150 ml of absolute tetrahydrofuran, are added dropwise. The mixture is boiled under reflux for 48 hours, 10 ml portions of water, 15% strength potassium hydroxide solution and again water are added dropwise, and the organic salts are filtered off with suction and extracted by boiling twice with tetrahydrofuran. The tetrahydrofuran solutions are concentrated, and the residue is distilled under high vacuum. 5.30 g (43.5% of theory) of the product are obtained

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. additionare added dropwise
  4. temperatureunder reflux for 48 hours
  5. filtrationthe organic salts are filtered off with suction
  6. extractionextracted
  7. concentrationThe tetrahydrofuran solutions are concentrated
  8. distillationthe residue is distilled under high vacuum
  9. custom5.30 g (43.5% of theory) of the product are obtained

Sources & evidence

ORD record
ord-29a3d6e0dca643e485207c9d6fad4dea
Source dataset
uspto-grants-2006_08
Patent number
US07091198B1

Reaction notes

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