Triphenylphosphine → tert-butyl 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate

HRID 1093172Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1093172
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Cl:15][C:16]1[N:21]=[C:20]2[NH:22][N:23]=[CH:24][C:19]2=[C:18]([N:25]2[CH2:31][CH:30]3[O:32][CH:27]([CH2:28][CH2:29]3)[CH2:26]2)[N:17]=1.O[CH:34]1[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36][CH2:35]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH:27]12[O:32][CH:30]([CH2:29][CH2:28]1)[CH2:31][N:25]([C:18]1[N:17]=[C:16]([Cl:15])[N:21]=[C:20]3[N:22]([CH:34]4[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36][CH2:35]4)[N:23]=[CH:24][C:19]=13)[CH2:26]2

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 201118843-(6-chloro-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane

Produkt 1

HCID 86629367tert-butyl 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Diisopropyl azodicarboxylate (0.71 mL, 3.6 mmol) was added in drops to a suspension of 3-(6-chloro-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane (0.53 g, 2.0 mmol), tert-butyl 4-hydroxy-1-piperidinecarboxylate (0.48 g, 2.4 mmol), and triphenylphosphine (0.79 g, 3.0 mmol) in tetrahydrofuran (20 mL). After stirring at room temperature for 16 hours, the mixture was adsorbed onto flash silica gel and purified by automated flash chromatography (hexanes/ethyl acetate) to provide tert-butyl 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate as a white solid contaminated with a light yellow material (0.81 g, 90%). MS (ES+): 448.9, 450.2 (M+H)+

Aufarbeitung

  1. custompurified by automated flash chromatography (hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-b4e2110122254968996bacb929eac4bd
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129371B2

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