Eserethole → HCID 14349816, compound

HRID 1078316Notes

Reaction equation

HRID 1078316 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-6909a113bd7f43479033ee2bbfa7b780
Source dataset
uspto-grants-1996_08
Patent number
US05547977

Reaction notes

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