Triphenylphosphine → HCID 69252373, Verbindung

HRID 902700Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 902700
[Cl:1][C:2]1[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]([CH2:10][CH:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][CH2:7][CH2:8][OH:9].[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][N:42]([C:45]2[CH:50]=[CH:49][CH:48]=[C:47](O)[CH:46]=2)[CH2:41][CH2:40]1)=[O:38])([CH3:35])([CH3:34])[CH3:33].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][N:42]([C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([O:9][CH2:8][CH2:7][CH2:6][N:5]([CH2:4][C:3]3[CH:24]=[CH:25][CH:26]=[C:27]([C:28]([F:29])([F:30])[F:31])[C:2]=3[Cl:1])[CH2:10][CH:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:46]=2)[CH2:41][CH2:40]1)=[O:38])([CH3:35])([CH3:33])[CH3:34]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 18669061tert-Butyl 4-(3-hydroxyphenyl)piperazine-1-carboxylateHCID 577571173-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propan-1-ol

Produkt 1

HCID 69252373HCID 69252373, VerbindungAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirring solution of 3-[(2-chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-amino]-propan-1-ol (448 mg, 1.0 mmol) in toluene (30 mL) was added 4-(3-hydroxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (419 mg, 1.50 mmol). Polymer bound triphenylphosphine (500 mg, 1.50 mmol, 3 mmol/g, Fluka Chemie) was then added, and the mixture stirred for 15 minutes. The reaction mixture was then cooled to 0° C. and diisopropylazodicarboxylate (303 mg, 1.50 mmol) was added in a dropwise fashion. After stirring at room temperature overnight, the crude reaction mixture was filtered and the solid washed with toluene. Concentration of the filtrate in vacuo followed by purification by flash silica gel chromatography (silica gel 60, EM science; 15% EtOAc:hexane) afforded title compound as an oil (0.59 g, 84%). MS(ES) m/e 708.4 (M+).

Aufarbeitung

  1. additionwas then added
  2. stirringAfter stirring at room temperature overnight
  3. customthe crude reaction mixture
  4. filtrationwas filtered
  5. washthe solid washed with toluene
  6. customConcentration of the filtrate in vacuo followed by purification by flash silica gel chromatography (silica gel 60, EM science; 15% EtOAc:hexane)

Quellen und Nachweise

ORD-Eintrag
ord-66198db799b84ca5a66e43faee1ac1b2
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365085B2

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