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

HRID 449703Notes

Reaction equation

HRID 449703 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 an 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-f92acff430b64b739ac0ef8dcf092b11
Source dataset
uspto-grants-2013_07
Patent number
US08481540B2

Reaction notes

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