m-Chloroperbenzoic acid → 1154759-69-9

HRID 577722Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 0 °C

Procedure

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)

Workup

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)

Sources & evidence

ORD record: ord-31a9ba636d8046198ace0f8864d2cddf
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040547B2

Reaction notes

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