2-Methyltetrahydrofuran → {(4-Cyano-2-methylsulfanyl-phenyl)-[6-oxo-2-(3-trifluoromethyl-phenylamino)cyclohex-1-enyl]-methyl}-carbamic acid tert-butyl ester

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Reaction Steps

Sodium hydride (60% in mineral oil, 154 mg, 3.85 mmol) is added in portions to a mixture of 3-(3-trifluoromethyl-phenylamino)-cyclohex-2-enone (INTERMEDIATE 3; 960 mg, 3.76 mmol) and 2-methyltetrahydrofuran (8 mL). After 30 min [benzenesulfonyl-(4-cyano-2-methylsulfanyl-phenyl)-methyl]-carbamic acid tert-butyl ester (Step 1, 1.56 g, 3.73 mmol) is added and the mixture is stirred at room temperature for 50 min. Water and 2-methyltetrahydrofuran are added and the phases are separated. The organic phase is dried over Na2SO4 and concentrated under reduced pressure. Yield: 2.13 g. ESI mass spectrum: [M+H]+=532; Retention time HPLC: 1.22 min (Z018_S04).

Provenance & Evidence