Hydrochloric Acid → (R)-[1-(2-hydroxy-ethyl)-4,5,6,7-tetrahydro-1H-indazol-4-yl]-carbamic acid benzyl ester

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Reaktionsgleichung

C([O:3][C:4](=O)[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:15][C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[C:9]=2[CH:8]=[N:7]1)C.[BH4-].[Na+].Cl>CO>[CH2:19]([O:18][C:16](=[O:17])[NH:15][C@@H:10]1[CH2:11][CH2:12][CH2:13][C:14]2[N:6]([CH2:5][CH2:4][OH:3])[N:7]=[CH:8][C:9]1=2)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

To a solution of ((R)-4-benzyloxycarbonylamino-4,5,6,7-tetrahydro-indazol-1-yl)-acetic acid ethyl ester (2.00 g, 5.60 mmol) in methanol (150 mL) was added sodium borohydride (1.61 g, 39.5 mmol). The mixture was stirred at 70° C. for 2 hours. After being cooled to room temperature, the reaction mixture was acidified to pH 7 with 5N hydrochloric acid, and then concentrated to remove methanol. The resulting mixture was extracted with dichloromethane (20 mL). After filtering out any insoluble materials from the organic layer, the filtrate was concentrated in vacuo to give [(R)-1-(2-hydroxy-ethyl)-4,5,6,7-tetrahydro-1H-indazol-4-yl]-carbamic acid benzyl ester (1.68 g, 95%) as a white solid. MS calcd. for C17H21N3O3 315, obsd. (ESI+) [(M+H)+] 316.

Aufarbeitung

temperatureAfter being cooled to room temperature
concentrationconcentrated
customto remove methanol
extractionThe resulting mixture was extracted with dichloromethane (20 mL)
filtrationAfter filtering out any insoluble materials from the organic layer
concentrationthe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-3dcf8c29e4cd40e4a763ab4687e4cbb2
Quelldatensatz: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08420675B2

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