Water → HCID 86698017, compound

HRID 518864Notes

Reaction equation

HRID 518864 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH:12]([CH3:14])[CH3:13])[CH:3]=1.[N:15]12[CH2:23][CH2:22][CH2:21][C@@H:20]1[CH2:19][NH:18][CH2:17][CH2:16]2.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:18]2[CH2:17][CH2:16][N:15]3[CH2:23][CH2:22][CH2:21][C@@H:20]3[CH2:19]2)=[CH:3][C:4]=1[O:11][CH:12]([CH3:14])[CH3:13])([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 7004239(8aR)-Octahydropyrrolo(1,2-a)pyrazineHCID 106318324-Fluoro-2-isopropoxy-1-nitrobenzene

Product 1

HCID 86698017HCID 86698017, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 1.0 g of 4-fluoro-1-nitro-2-(propan-2-yloxy)benzene, 634 mg of (R)-1,4-diazabicyclo[4,3,0]nonane and 1.04 g of potassium carbonate in 7 ml of DMSO is stirred at ambient temperature for 21 hours. The reaction medium is run into 15 ml of water and the mixture is then extracted three times with 30 ml of ethyl acetate. The organic phases are dried over magnesium sulfate, filtered and concentrated under vacuum, so as to obtain 1.44 g of (8aR)-2-[4-nitro-3-(propan-2-yloxy)phenyl]octahydropyrrolo[1,2-a]pyrazine in the form of an orangey-coloured oily residue.

Workup

  1. extractionthe mixture is then extracted three times with 30 ml of ethyl acetate
  2. dry with materialThe organic phases are dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-88bc5cc7acb949cb9454896c9bd811cf
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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