m-Chloroperbenzoic acid → tert-butyl N-(1-oxaspiro(2.3)hexan-5-yl)carbamate

HRID 577722Notizen

Reaktionsgleichung

[C:1]([O:5][C:6](=[O:13])[NH:7][CH:8]1[CH2:11][C:10](=[CH2:12])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:22])C=1>ClCCl>[C:1]([O:5][C:6](=[O:13])[NH:7][CH:8]1[CH2:9][C:10]2([O:22][CH2:12]2)[CH2:11]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A solution of (3-methylene-cyclobutyl)-carbamic acid tert-butyl ester (4.27 g, 23.3 mmol) in dichloromethane (95 mL) was cooled to 0° C. in an ice/water bath. 3-Chloroperbenzoic acid (77% technical grade, 5.84 g, 26 mmol) was added in small portions. After stirring at 0° C. for 1.5 hours, the mixture was transferred to a separatory funnel and washed sequentially with 10% aqueous Na2SO3 (50 mL), saturated aqueous NaHCO3 (30 mL), and saturated aqueous NaCl (30 mL). The organic layer was dried over magnesium sulfate, filtered, concentrated, and purified by silica gel chromatography (eluting with 30-100% ethyl acetate in heptane), affording the title compound (2.84 g, 61%) as a white solid. NMR showed a 1:1 mixture of N,O-cis/trans isomers. 1H NMR (400 MHz, chloroform-d) δ ppm 1.46 (d, J=1.26 Hz, 9H) 2.35-2.45 (m, 2H) 2.67-2.83 (m, 4H) 3.97-4.36 (m, 1H) 4.77 (br. s., 1H)

Aufarbeitung

customthe mixture was transferred to a separatory funnel
washwashed sequentially with 10% aqueous Na2SO3 (50 mL), saturated aqueous NaHCO3 (30 mL), and saturated aqueous NaCl (30 mL)
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
custompurified by silica gel chromatography (eluting with 30-100% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag: ord-31a9ba636d8046198ace0f8864d2cddf
Quelldatensatz: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09040547B2

Notizen zur Reaktion

Wird geladen…