Triethylamine → Tert-butyl 8-(6-nitropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane-3-carboxylate

HRID 449566Notes

Reaction equation

C(N(CC)CC)C.F[C:9]1[CH:10]=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[N:13][CH:14]=1.[C@@H:18]12[NH:25][C@@H:22]([CH2:23][CH2:24]1)[CH2:21][N:20]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:19]2>CS(C)=O.C(OCC)(=O)C>[N+:15]([C:12]1[N:13]=[CH:14][C:9]([N:25]2[CH:18]3[CH2:24][CH2:23][CH:22]2[CH2:21][N:20]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:19]3)=[CH:10][CH:11]=1)([O-:17])=[O:16]

Participants

Conditions

Temperature: 80 °C

Procedure

Triethylamine (6.87 mL, 49.3 mmol) was added to a stirred solution of 5-fluoro-2-nitropyridine (700 mg, 4.93 mmol) and (1R,5S)-tert-butyl 3,8-diazabicyclo[3.2.1]octane-3-carboxylate (1.05 g, 4.93 mmol) in 8 mL of DMSO at room temperature. The reaction mixture was heated to 80° C. for 2 hr. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed with, saturated ammonium chloride, water (3×), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford 1.21 g (73.5%) of tert-butyl 8-(6-nitropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane-3-carboxylate as yellow solid.

Workup

temperatureAfter cooling to room temperature
washwashed with, saturated ammonium chloride, water (3×)
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-1b78ddc65e75436eb5e758a108f49230
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481540B2

Reaction notes

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