Triethylamine → (1R,5S)-3-methyl-8-(6-nitropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane

HRID 1431195Notes

Reaction equation

HRID 1431195 reaction equation
Cl.Cl.[CH3:3][N:4]1[CH2:10][C@H:9]2[NH:11][C@H:6]([CH2:7][CH2:8]2)[CH2:5]1.F[C:13]1[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[N:17][CH:18]=1.C(N(CC)CC)C>CS(C)=O.CCOC(C)=O>[CH3:3][N:4]1[CH2:10][C@H:9]2[N:11]([C:13]3[CH:18]=[N:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=3)[C@H:6]([CH2:7][CH2:8]2)[CH2:5]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 167481095-Fluoro-2-nitropyridineHCID 66743274(1R,5S)-3-Methyl-3,8-diazabicyclo[3.2.1]octane dihydrochloride

Product 1

HCID 66742801(1R,5S)-3-methyl-8-(6-nitropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octaneYield 81.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (1R,5S)-3-Methyl-3,8-diazabicyclo[3.2.1]octane dihydrochloride (981 mg, 4.93 mmol), 5-fluoro-2-nitropyridine (100 mg, 4.93 mmol), and triethylamine (4.99 g, 49.3 mmol) in DMSO (8 ml) was heated to 80° C. for 2 hr. After cooling to room temperature, the reaction mixture was diluted with EtOAc and washed with saturated ammonium chloride, and water. The organic phase was then concentrated and triturated with ether to give desire product as a yellow solid (1 g, 81.8%).

Workup

  1. washwashed with saturated ammonium chloride, and water
  2. concentrationThe organic phase was then concentrated
  3. customtriturated with ether

Sources & evidence

ORD record
ord-300b9b288a2142a29c1b9d2f9429c9e8
Source dataset
uspto-grants-2015_01
Patent number
US08940741B2

Reaction notes

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