4-Methylmorpholine → HCID 68643966, compound

HRID 2388694Notes

Reaction equation

HRID 2388694 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN1CCOCC1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[C:41]([O:45][C:46]([N:48]1[CH2:53][CH2:52][C:51]2[O:54][N:55]=[C:56]([C:57](O)=[O:58])[C:50]=2[CH2:49]1)=[O:47])([CH3:44])([CH3:43])[CH3:42]>CN(C)C=O>[N:1]1([C:57]([C:56]2[C:50]3[CH2:49][N:48]([C:46]([O:45][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:47])[CH2:53][CH2:52][C:51]=3[O:54][N:55]=2)=[O:58])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 8082PiperidineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 576186225-(1,1-Dimethylethyl) 6,7-dihydroisoxazolo[4,5-c]pyridine-3,5(4H)-dicarboxylate

Product 1

HCID 68643966HCID 68643966, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Piperidine (1.1 ml, 11.18 mmol), N-methylmorpholine (3.68 ml, 33.54 mmol) and BOP reagent (6.42 g, 14.53 mmol) were added to a solution of 5-(tert-butoxycarbonyl)-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxylic acid (3 g, 11.18 mmol) in dry dimethylformamide (100 ml) and the reaction mixture was stirred at room temperature for 16 hours. The solution was then concentrated in vacuo, the residue was taken up in ethyl acetate and the mixture was washed with NaHCO3 solution and NaCl solution. The combined organic phases were dried with Na2SO4, filtered and concentrated in vacuo. Purification was carried out by chromatography on silica gel (100-200 mesh silica gel, 30% ethyl acetate in hexane). The yield was (71%).

Workup

  1. concentrationThe solution was then concentrated in vacuo
  2. washthe mixture was washed with NaHCO3 solution and NaCl solution
  3. dry with materialThe combined organic phases were dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification

Sources & evidence

ORD record
ord-5fa2baff715a4f97a340fc10e99c5e43
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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