Diisopropylethylamine → 1-{[3-(4-Methylphenyl)isoxazol-4-yl]carbonyl}-3-phenylpyrrolidin-3-ol

HRID 1446278

Reaktionsgleichung

Reaktionsgleichung von HRID 1446278
[C:1]1([C:7]2([OH:12])[CH2:11][CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.[CH3:44][C:45]1[CH:50]=[CH:49][C:48]([C:51]2[C:55]([C:56](O)=[O:57])=[CH:54][O:53][N:52]=2)=[CH:47][CH:46]=1>CN(C=O)C>[CH3:44][C:45]1[CH:46]=[CH:47][C:48]([C:51]2[C:55]([C:56]([N:9]3[CH2:10][CH2:11][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)([OH:12])[CH2:8]3)=[O:57])=[CH:54][O:53][N:52]=2)=[CH:49][CH:50]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 2002813-Phenylpyrrolidin-3-olHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 588287973-(4-Methylphenyl)isoxazole-4-carboxylic acid

Produkt 1

HCID 591701901-{[3-(4-Methylphenyl)isoxazol-4-yl]carbonyl}-3-phenylpyrrolidin-3-olAusbeute 58,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3-phenylpyrrolidin-3-ol (8 mg, 0.039 mmol), TBTU (15 mg, 0.047 mmol, 1.2 equ.) and N-ethyl-N-isopropylpropan-2-amine (14 μL, 0,079 mmol, 2 equ.) in DMF (0.3 mL) was added to 3-(4-methylphenyl)isoxazole-4-carboxylic acid (8 mg, 0.039 mmol) and the reaction mixture was stirred at rt for 2 h. The solvent was evaporated and the crude product was purified by RP-HPLC. After evaporation of the solvents the product was dried in vacuum to yield the title compound (8 mg). MS (ESI, pos. ion) m/z Calcd for C21H20N2O3: 348.1474, found 348.1465.

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe crude product was purified by RP-HPLC
  3. customAfter evaporation of the solvents the product
  4. customwas dried in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3a717426d9714317980d439e8ff5a01e
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666888B2

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