Pyrrolidine → (5,5-Dimethyl-8-nitro-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl)-pyrrolidin-1-yl-methanone

HRID 1041590Notes

Reaction equation

[N+](C1C=CC([O:10][C:11]([N:13]2[CH2:19][CH2:18][CH2:17][C:16]([CH3:21])([CH3:20])[C:15]3[CH:22]=[CH:23][C:24]([N+:26]([O-:28])=[O:27])=[CH:25][C:14]2=3)=O)=CC=1)([O-])=O.[NH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1>O1CCCC1>[CH3:21][C:16]1([CH3:20])[CH2:17][CH2:18][CH2:19][N:13]([C:11]([N:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)=[O:10])[C:14]2[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:15]1=2

Participants

Conditions

Temperature: 60 °C

Procedure

5,5-Dimethyl-8-nitro-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid 4-nitro-phenyl ester (0.442 g, 0.00115 mol), pyrrolidine (1.090 mL, 0.013 mol) and anhydrous tetrahydrofuran (10 mL) were combined in a round bottom flask and heated to 60° C. for 23 hours. The reaction was concentrated under reduced pressure, then purified by normal phase chromatography to yield an off-white solid, (5,5-Dimethyl-8-nitro-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl)-pyrrolidin-1-yl-methanone (0.364 g, 78%). LCMS: m/z=318.15 (M+H+), 1H NMR (400 MHz, CDCl3) δ 7.97 (m, 1H), 7.87 (m, 1H), 7.60 (d, 1H, J=8.8 Hz), 3.10 (br s, 4H), 1.89 (br s, 2H), 1.73 (m, 6H), 1.47 (s, 6H).

Workup

concentrationThe reaction was concentrated under reduced pressure
custompurified by normal phase chromatography

Sources & evidence

ORD record: ord-a733533ef59e40b8a10c33299bce8d08
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552186B2

Reaction notes

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