4-Methylmorpholine → HCID 68644010, compound

HRID 2388705Notes

Reaction equation

HRID 2388705 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[O:14][N:15]=[C:16]([C:17](O)=[O:18])[C:10]=2[CH:9]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN([P+](ON1N=[N:44][C:39]2C=[CH:41][CH:42]=[CH:43][C:38]1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.N1CCCCC1>CN(C=O)C.O>[C:20]1([CH:9]2[C:10]3[C:16]([C:17]([N:44]4[CH2:41][CH2:42][CH2:43][CH2:38][CH2:39]4)=[O:18])=[N:15][O:14][C:11]=3[CH2:12][CH2:13][N:8]2[C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 8082PiperidineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 68644004HCID 68644004, compound

Product 1

HCID 68644010HCID 68644010, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 5-(tert-butoxycarbonyl)-4-phenyl-4,5,6,7-tetrahydroisoxazolo-[4,5-c]pyridine-3-carboxylic acid (1.747 mmol, 1.0 eq.) in DMF (2 ml) was added BOP reagent (2.27 mmol, 1.3 eq.) and N-methyl morpholine (5.24 mmol, 3.0 eq.). The reaction mixture was stirred at room temperature for 15 min. A solution of piperidine (1.747 mmol, 1.0 eq.) in DMF (0.5 ml) was added to the reaction mixture and it was stirred for 12 h. The mixture was poured into water and resulting aqueous solution was extracted with ethyl acetate. The organic layer was successively washed with water and brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure to give the crude product which was purified by column chromatography (silica). Yield: 23%.

Workup

  1. stirringwas stirred for 12 h
  2. customresulting aqueous solution
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was successively washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-46a0e9ab2c6f4f09b0f0d4f82f815bf2
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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