Triethylamine → (3S,5S)-1-(3-Amino-4-nitrophenyl)-N,N,5-trimethyl-3-pyrrolidinamine

HRID 1830008Notes

Reaction equation

[CH3:1][N:2]([CH3:9])[C@@H:3]1[CH2:7][NH:6][C@@H:5]([CH3:8])[CH2:4]1.[NH2:10][C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[C:13](F)[CH:12]=1.CCN(CC)CC>CN1CCCC1=O.O>[CH3:1][N:2]([CH3:9])[C@@H:3]1[CH2:7][N:6]([C:13]2[CH:12]=[C:11]([NH2:10])[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=2)[C@@H:5]([CH3:8])[CH2:4]1

Participants

Conditions

Temperature: 100 °C

Procedure

(2S,4S)-4-dimethylamino-2-methylpyrrolidine (1.0 equivalent) and 1-amino-3-fluoro-6-nitrobenzene (1.2 equivalents) were dissolved in N-methylpyrrolidinone, and Et3N (5.0 equivalents) was added. The solution was heated for 5 hours at 100° C. The solution was then cooled and diluted with water. The aqueous layer was extracted with ethyl acetate. The organic layer was then washed twice with H2O, once with brine, dried over Na2SO4, filtered, and concentrated. The crude material was purified by column chromatography (1:1 ethyl acetate:hexane to 1:20 MeOH:ethyl acetate to 1:1 MeOH: ethyl acetate to give the title compound as a yellow gum. LC/MS (m/z) 265.2 (MH+), Rt 1.65 minutes.

Workup

temperatureThe solution was then cooled
extractionThe aqueous layer was extracted with ethyl acetate
washThe organic layer was then washed twice with H2O, once with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude material was purified by column chromatography (1:1 ethyl acetate

Sources & evidence

ORD record: ord-99713da752154ee3ae44e1a696ca9383
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07064215B2

Reaction notes

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