Methyl iodide → HCID 178502727, Verbindung

HRID 25576

Reaktionsgleichung

[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14](=[O:19])[N:15]([O:17][CH3:18])[CH3:16])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:24].OS([O-])(=O)=O.[K+]>CN(C=O)C.O.CCOCC>[C:1]([O:5][C:6](=[O:20])[N:7]([C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14](=[O:19])[N:15]([O:17][CH3:18])[CH3:16])[CH2:10][CH2:9]1)[CH3:24])([CH3:4])([CH3:2])[CH3:3]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A solution of 24.18 g (82 mmol) of trans-[4-(Methoxy-methyl-carbamoyl)-cyclohexyl]-carbamic acid tert-butyl ester in 80 ml of DMF was treated at 0° C. with 5.37 g (123 mmol) of 55% NaH in small portions. The reaction was stirred for 1 h at 0° C., then treated slowly (20 min) with 40.9 ml (656 mmol) iodomethane and warmed up to RT over night. The reaction is cooled and neutralized with aqueous 10% KHSO4 and poured into water/Et2O (3×). The organic phase was washed with aqueous 10% NaCl, dried over Na2SO4 evaporated and purified by flash silica gel column (CH2Cl2/EtOAc 9:1 to 1:1) to yield 20.69 g (84%) of trans-[4-(Methoxy-methyl-carbamoyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester, MS: 301 (MH+).

Aufarbeitung

temperaturewarmed up to RT over night
temperatureThe reaction is cooled
washThe organic phase was washed with aqueous 10% NaCl
dry with materialdried over Na2SO4
customevaporated
custompurified by flash silica gel column (CH2Cl2/EtOAc 9:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag: ord-168197dfb0dd44c3abd2b6d9f145f2ee
Quelldatensatz: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06858651B2

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