Water → 3-(Naphth-2-yl)-8-azabicyclo[3.2.1]octane oxalate

HRID 1871913Notes

Reaction equation

HRID 1871913 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]1[CH2:17][CH:16]2[N:18](C([O:21][CH2:22][CH3:23])=O)[CH:13]([CH2:14][CH2:15]2)[CH2:12]1.[OH2:24].NN.[OH-:27].[K+].[OH2:29]>C(O)CO>[C:22]([OH:21])(=[O:29])[C:23]([OH:27])=[O:24].[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]1[CH2:17][CH:16]2[NH:18][CH:13]([CH2:14][CH2:15]2)[CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 186899083-(Naphth-2-yl)-8-ethoxycarbonyl-8-azabicyclo[3.2.1]octane

Product 1

HCID 186899233-(Naphth-2-yl)-8-azabicyclo[3.2.1]octane oxalate

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A mixture of 2.64 gm (8.53 mMol) 3-(naphth-2-yl)-8-ethoxycarbonyl-8-azabicyclo[3.2.1]octane, 2.14 gm (42.7 mMol) hydrazine hydrate, and 2.87 gm (51.2 mMol) potassium hydroxide in 70 mL ethylene glycol was heated at reflux for 2 hours. The reaction mixture was allowed to cool gradually to room temperature, poured into water and extracted well with diethyl ether. The organic phase was dried over sodium sulfate and concentrated under reduced pressure. The residue was treated with oxalic acid to provide the title compound.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. extractionextracted well with diethyl ether
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionThe residue was treated with oxalic acid

Sources & evidence

ORD record
ord-5f3e389611c5448696ab82620b362106
Source dataset
uspto-grants-2000_08
Patent number
US06107307

Reaction notes

Loading…