Morpholine → HCID 12074073, compound

HRID 413926Notes

Reaction equation

HRID 413926 reaction equation
C([O:4][C:5](=[O:29])[C@@H:6]([CH2:26][O:27][CH3:28])[CH2:7][C@H:8]([NH:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=1)=[O:17])[CH2:9][O:10][CH2:11][O:12][CH2:13][CH3:14])C=C.N1CCOCC1>C1COCC1.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:13]([O:12][CH2:11][O:10][CH2:9][C@@H:8]([NH:15][C:16]([C:18]1[CH:19]=[CH:20][C:21]([C:24]#[N:25])=[CH:22][CH:23]=1)=[O:17])[CH2:7][C@H:6]([CH2:26][O:27][CH3:28])[C:5]([OH:29])=[O:4])[CH3:14]

Participants

6

Reactant 2

HCID 8083MorpholineHCID 12074072HCID 12074072, compound

Product 1

HCID 12074073HCID 12074073, compoundYield 101.8%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of the compound prepared in Example 5 (1.45 g) and morpholine (0.38 ml) in THF (3.6 ml), tetrakis(triphenylphosphine) palladium(0) (20 mg) was added, and the mixture was stirred for 3 hours at room temperature. The reaction mixture was diluted with ethyl acetate, and washed with 1N aqueous solution of hydrochloride and a saturated aqueous solution of sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and concentrated to give the title compound (1.33 g) having the following physical data.

Workup

  1. washwashed with 1N aqueous solution of hydrochloride
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ba726998b64848288ed7f43da5fad4e2
Source dataset
uspto-grants-2003_05
Patent number
US06569899B1

Reaction notes

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