Water → 2-(cyclohexylphenylamino)-N-(1,3,3-trimethylbicyclo[2.2.1]hept-2-yl)acetamide

HRID 51290

Reaktionsgleichung

[CH:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Cl[CH2:25][C:26]([NH:28][CH:29]1[C:34]([CH3:36])([CH3:35])[CH:33]2[CH2:37][C:30]1([CH3:38])[CH2:31][CH2:32]2)=[O:27].O>O1CCCC1>[CH:8]1([N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:25][C:26]([NH:28][CH:29]2[C:34]([CH3:36])([CH3:35])[CH:33]3[CH2:37][C:30]2([CH3:38])[CH2:31][CH2:32]3)=[O:27])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of N-cyclohexylaniline (100 mg, 0.56 mmol) in tetrahydrofuran (4 ml) at −78° C. was added LiHMDS (1 ml of a 1M solution in tetrahydrofuran) dropwise. The solution was allowed to warm to 0° C., then recooled to −78° C., and a solution of 2-chloro-N-(1,3,3-trimethylbicyclo[2,2,1]hept-2-yl)acetamide (124 mg, 0.56 mmol) in tetrahydrofuran (1 ml) added dropwise. The mixture was allowed to warm to room temperature, and was stirred for 1 hour. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulfate. The ethyl acetate solution was absorbed onto silica gel, which was eluted with 3% methanol/methylene chloride, to yield 2-(cyclohexylphenylamino)-N-(1,3,3-trimethylbicyclo[2.2.1]hept-2-yl)acetamide.

Aufarbeitung

customrecooled to −78° C.
temperatureto warm to room temperature
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over magnesium sulfate
customThe ethyl acetate solution was absorbed onto silica gel, which
washwas eluted with 3% methanol/methylene chloride

Quellen und Nachweise

ORD-Eintrag: ord-426cb6d8cdc74b3997412c5c983e5829
Quelldatensatz: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06713650B2

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