Triphenylphosphine → (3-(Tert-butoxycarbonylamino)propoxy]-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

HRID 21099

Reaktionsgleichung

Reaktionsgleichung von HRID 21099
O[C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:34].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:54][CH2:55][CH2:56][CH2:57][NH:58][C:59](=[O:65])[O:60][C:61]([CH3:64])([CH3:63])[CH3:62].CCOC(/N=N/C(OCC)=O)=O.C1(C)C=CC=CC=1>C1COCC1>[C:61]([O:60][C:59]([NH:58][CH2:57][CH2:56][CH2:55][O:54][N:5]1[CH2:4][C:3]2[C:7](=[C:8]([C:11]3[N:12]([C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28])[C:13]4[C:18]([CH:19]=3)=[CH:17][C:16]([CH2:20][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:15][CH:14]=4)[CH:9]=[CH:10][CH:2]=2)[C:6]1=[O:34])=[O:65])([CH3:64])([CH3:63])[CH3:62]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 3838134tert-butyl N-(3-hydroxypropyl)carbamateHCID 684932224-Hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinoneHCID 87147022ethyl (NE)-N-ethoxycarbonyliminocarbamate;toluene

Produkt 1

HCID 86628231(3-(Tert-butoxycarbonylamino)propoxy]-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinoneAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a similar manner to Step 1 of Example 149, 4-hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (60.0 mg, 0.130 mmol) was dissolved in THF (3.6 mL), and the solution was treated with triphenylphosphine (136 mg, 0.78 mmol), tert-butyl N-(3-hydroxypropyl)carbamate (92 mg, 0.52 mmol) and 40% DEAD-toluene solution (0.236 mL), followed by purification by preparative thin-layer chromatography (chloroform/methanol=4/1) to obtain 4-[(3-(tert-butoxycarbonylamino)propoxy]-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (70.5 mg, yield 88%).

Aufarbeitung

  1. customfollowed by purification by preparative thin-layer chromatography (chloroform/methanol=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-c79fe87ae548425b8f2fbe23a7c07ff0
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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