Sodium Hydroxide → HCID 86739997, compound

HRID 1381156Notes

Reaction equation

HRID 1381156 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 98.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3.56 L 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-5490bd439a1f4617a62c46f0e1744be3
Source dataset
uspto-grants-1986_04
Patent number
US04585779

Reaction notes

Loading…