Sodium Hydroxide → HCID 86739997, compound

HRID 463874Notes

Reaction equation

HRID 463874 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][C@@H:9]2[O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C@@H:8]2[CH2:7]1)=O)C.[OH-].[Na+]>C(O)C>[C:13]1([C@@:9]23[O:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[C@@H:8]2[CH2:7][NH:6][CH2:11][CH2:10]3)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86739998HCID 86739998, compound

Product 1

HCID 86739997HCID 86739997, compoundYield 150.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3.56 g of cis-2-ethoxycarbonyl-1,2,3,4,4a,9b-hexahydro-benzofuro[3,2-c]pyridine in 42 ml of absolute ethanol was added 28 ml of 20% aqueous NaOH solution. The resulting mixture was heated at reflux under nitrogen for 32 hours. Most of the ethanol was removed in vacuo. The residue was diluted with 50 ml of water and extracted with methylene chloride (2×100 ml). There were initially some problems with emulsions. The combined extracts were dried over anhydrous Na2SO4 and evaporated in vacuo to give 2.72 g (98.4%) of crystalline solid. Recrystallization from hexane afforded 1.98 g (71.6%) of crystals, m.p. s 91, 95°-98°.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux under nitrogen for 32 hours
  3. customMost of the ethanol was removed in vacuo
  4. additionThe residue was diluted with 50 ml of water
  5. extractionextracted with methylene chloride (2×100 ml)
  6. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-d8aebb39236e45b4ac0701e77bc8edcc
Source dataset
uspto-grants-1985_10
Patent number
US04544745

Reaction notes

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