Benzyl Alcohol → 4-Benzyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

HRID 21124

Reaktionsgleichung

Reaktionsgleichung von HRID 21124
[OH:1][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.[CH2:54](O)[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1.CCOC(/N=N/C(OCC)=O)=O.C1(C)C=CC=CC=1>C1COCC1>[CH2:54]([O:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[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])[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1

Komponenten

6

Edukt 4

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 684932224-Hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinoneHCID 87147022ethyl (NE)-N-ethoxycarbonyliminocarbamate;toluene

Produkt 1

HCID 684909864-Benzyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinoneAusbeute 73,3 %

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 (80.0 mg, 0.173 mmol) was dissolved in THF (4.0 mL), and the solution was treated with triphenylphosphine (137 mg, 0.519 mmol), benzylalcohol (0.0534 mL, 0.519 mmol) and 40% DEAD-toluene solution (0.237 mL), followed by purification by flash column chromatography (chloroform/methanol=100/0 to 90/10) to obtain 4-benzyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (70 mg, yield 73%).

Aufarbeitung

  1. customfollowed by purification by flash column chromatography (chloroform/methanol=100/0 to 90/10)

Quellen und Nachweise

ORD-Eintrag
ord-36103d8e803747e7b9a9675e25fddaa3
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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