HCID 15703044, compound → HCID 15703035, compound

HRID 1087951Notes

Reaction equation

HRID 1087951 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][C:5]1([CH2:23][CH3:24])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH2:8][CH2:7][O:6]1)=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=3>C(O)C.[OH-].[Na+]>[CH2:23]([C:5]1([CH2:4][C:3]([OH:25])=[O:2])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH2:8][CH2:7][O:6]1)=[CH:16][C:15]([O:18][C:19]([F:21])([F:20])[F:22])=[CH:14][CH:13]=3)[CH3:24]

Participants

4

Reactant 1

HCID 15703044HCID 15703044, compound

Product 1

HCID 15703035HCID 15703035, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 1-ethyl-1,3,4,9-tetrahydro-6-(trifluoromethoxy)pyrano[3,4-b]indole-1-acetic acid methyl ester (6.2 g, 17.4 mmol) in ethanol (80 mL) and 2.5N NaOH (24 mL) was stirred at ambient temperature under nitrogen for 3 hours. The ethanol was removed in vacuo and the residue was diluted with H2O (70 mL) and washed with ether. The aqueous phase was acidified (to pH3) with 2N-HCl and extracted with Et2O. The extract was washed with brine and dried (Na2SO4). Removal of the solvent afforded the crude product (5.2 g, amber oil). Crystallization from Et2O-hexane gave 3.43 g of the pure title compound (mp 148° C., white solid). A second crop was obtained from the mother liquor (0.54 g, mp 148° C., light brown solid). The combined yield was 67%.

Workup

  1. customThe ethanol was removed in vacuo
  2. additionthe residue was diluted with H2O (70 mL)
  3. washwashed with ether
  4. extractionextracted with Et2O
  5. washThe extract was washed with brine
  6. dry with materialdried (Na2SO4)
  7. customRemoval of the solvent
  8. customafforded the crude product (5.2 g, amber oil)
  9. customCrystallization from Et2O-hexane

Sources & evidence

ORD record
ord-e9a7525b83b2407b8d473ded8f70b3a5
Source dataset
uspto-grants-1990_10
Patent number
US04960902

Reaction notes

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