Diisobutylaluminum hydride → Tert-butyl ((4-(hydroxymethyl)oxazol-2-yl)methyl)carbamate

HRID 1157849

Reaktionsgleichung

C[O:2][C:3]([C:5]1[N:6]=[C:7]([CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[O:8][CH:9]=1)=O.CC(C[AlH]CC(C)C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>ClCCl>[C:15]([O:14][C:12](=[O:13])[NH:11][CH2:10][C:7]1[O:8][CH:9]=[C:5]([CH2:3][OH:2])[N:6]=1)([CH3:18])([CH3:16])[CH3:17]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

The ester (178 mg, 0.695 mmol) in 0° C. dichloromethane (8 mL) was treated with DIBAL-H (1 M in dichloromethane, 2.08 mL, 2.08 mmol). The mixture was then stirred at 0° C. for 2 hours before being treated with aqueous 5% sodium potassium tartrate (8 mL). The mixture was stirred rapidly for 30 minutes (until the aqueous and organic layers clarified), and the layers were then separated. The aqueous layer was extracted twice with dichloromethane. The combined organic fractions were then dried over anhydrous sodium sulfate and concentrated. Purification by chromatography on silica gel (5% methanol in dichloromethane) gave (4-hydroxymethyl-oxazol-2-ylmethyl)-carbamic acid tert-butyl ester as an oil (45 mg, 28%). 1H NMR (CDCl3) δ 1.40 (s, 9H), 4.43 (d, 2H, J=5.6 Hz), 4.56 (s, 2H), 5.37 (s, 1H), 7.54 (s, 1H).

Aufarbeitung

stirringThe mixture was stirred rapidly for 30 minutes (until the aqueous and organic layers
customwere then separated
extractionThe aqueous layer was extracted twice with dichloromethane
dry with materialThe combined organic fractions were then dried over anhydrous sodium sulfate
concentrationconcentrated
customPurification by chromatography on silica gel (5% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag: ord-f816e08cdf00484586c4294ef4fd71e8
Quelldatensatz: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07807694B2

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