Dichloromethane → 1,2,3,3a,8,8a-Hexahydro-5-nitro-1,3a,8-trimethylpyrrolo[2,3-b]indole

HRID 703535Notes

Reaction equation

[CH3:1][N:2]1[CH:6]2[N:7]([CH3:14])[C:8]3[C:13]([C:5]2([CH3:15])[CH2:4][CH2:3]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.F[B-](F)(F)F.[O:21]=[N+:22]=[O:23].C([O-])(O)=O.[Na+].C(Cl)Cl>C(#N)C>[N+:22]([C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:14])[CH:6]1[N:2]([CH3:1])[CH2:3][CH2:4][C:5]21[CH3:15])([O-:23])=[O:21]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole (25.0 g) in acetonitrile (500 ml) at 0° C. was added nitronium tetrafluoroborate (18.65 g) dissolved in acetonitrile (500 ml) in a dropwise manner over a period of 0.5 hour. The reaction mixture was stirred at 0° C. for 1 hour and allowed to warm to room temperature for an additional hour. Ice and a dilute NaHCO3 solution were added followed by methylene chloride (800 ml). The layers were separated and the aqueous layer was extracted with methylene chloride (2×200 ml). The organic layers were combined, dried (Na2SO4), and concentrated to give an oil which was chromatographed twice on silica gel, first eluting with 2.5% methanol/ethyl acetate and then with 2% methanol/methylene chloride to give 1,2,3,3a,8,8a-hexahydro-5-nitro-1,3a,8-trimethylpyrrolo[2,3-b]indole (7.7 g).

Workup

temperatureto warm to room temperature for an additional hour
customThe layers were separated
extractionthe aqueous layer was extracted with methylene chloride (2×200 ml)
dry with materialdried (Na2SO4)
concentrationconcentrated
customto give an oil which
customwas chromatographed twice on silica gel
washfirst eluting with 2.5% methanol/ethyl acetate

Sources & evidence

ORD record: ord-24a19bfa33e54a2ab5c664de2ebc2510
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04983616

Reaction notes

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