Red-Al → rac-(1R,2R,4R*)-2-{2-[methyl-(3-methylamino-propyl)-amino]-ethyl}-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol

HRID 220317

Reaktionsgleichung

C(O[C:6](=O)[NH:7][CH2:8][CH2:9][C:10](=O)[N:11]([CH2:13][CH2:14][C@:15]1([OH:29])[CH2:20][C@H:19]2[CH2:21][CH2:22][C@@H:16]1[CH:17]=[C:18]2[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:12])(C)(C)C.COCCO[AlH2-]OCCOC.[Na+]>C1COCC1>[CH3:12][N:11]([CH2:10][CH2:9][CH2:8][NH:7][CH3:6])[CH2:13][CH2:14][C:15]1([OH:29])[CH2:20][CH:19]2[CH2:21][CH2:22][CH:16]1[CH:17]=[C:18]2[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To a cold solution of 88 mg of rac-(2-{[2-((1R*,2R*,4R*)-2-hydroxy-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl)-ethyl]-methyl-carbamoyl}-ethyl)-carbamic acid tert.-butyl ester in 5 mL THF was added dropwise 0.5 mL Red-Al, 65% toluenel. The ice bath was removed and the reaction mixture was heated to 60° C. for 1.5 h. The reaction was cooled with an ice bath and quenched by careful addition of 1M NaOH. After stirring for 10 min, the 2 phases were separated and the organic phase was concentrated in vacuo to obtain 80 mg of crude rac-(1R*,2R*,4R*)-2-{2-[methyl-(3-methylamino-propyl)-amino]-ethyl}-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol as yellow oil.

Aufarbeitung

customThe ice bath was removed
temperatureThe reaction was cooled with an ice bath
customquenched by careful addition of 1M NaOH
customthe 2 phases were separated
concentrationthe organic phase was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-61154cda02254c1b918ca67b1a684e0f
Quelldatensatz: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08202885B2

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