Eserethole → HCID 14349816, compound

HRID 53894Notes

Reaction equation

HRID 53894 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[C@H:8]1[N:14]([CH3:17])[CH2:15][CH2:16][C@@:7]21[CH3:18])[CH3:2].F[B-](F)(F)F.[O:24]=[N+:25]=[O:26]>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:10](=[C:11]([N+:25]([O-:26])=[O:24])[CH:12]=1)[N:9]([CH3:13])[C@H:8]1[N:14]([CH3:17])[CH2:15][CH2:16][C@@:7]21[CH3:18])[CH3:2]

Participants

4

Reactant 2

HCID 10879418EseretholeHCID 11073463Nitronium tetrafluoroborate

Product 1

HCID 14349816HCID 14349816, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A degassed solution, under nitrogen, of 3.70 g of (3aS-cis)-5-ethoxy-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole in 50 ml of dry chloroform was treated with 2.00 g of nitronium tetrafluoroborate at a reaction temperature of +10°. After 20 minutes, the reaction was quenched by the addition of ice and saturated sodium bicarbonate solution with vigorous stirring. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated to an oil. This was purified by chromatography over silica gel using ethyl acetate as the eluent. The fractions containing the product were combined and concentrated to an oil which crystallized from hexane to afford crystals of pure (3aS-cis)-5-ethoxy-1,2,3,3a,8,8a- hexahydro-7-nitro-1,3a,8-trimethylpyrrolo[2,3-b]indole, mp 106°-108° C.

Workup

  1. customthe reaction was quenched by the addition of ice and saturated sodium bicarbonate solution with vigorous stirring
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated to an oil
  5. customThis was purified by chromatography over silica gel
  6. additionThe fractions containing the product
  7. concentrationconcentrated to an oil which
  8. customcrystallized from hexane

Sources & evidence

ORD record
ord-60c6f71afbf44f38993b496876186831
Source dataset
uspto-grants-1997_04
Patent number
US05621114

Reaction notes

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