Caprolactam → 2H-Azepine, 3,4,5,6-tetrahydro-7-methoxy-

To a solution of azepan-2-one (1.13 g, 10.0 mmol) in DCM (10 mL) in a 40 mL screw cap vial was added freshly prepared trimethyloxonium tetrafluoroborate (1.57 g, 10.59 mmol). The resulting suspension was shaken overnight. The reaction was quenched by the addition of saturated aqueous NaHCO3 (5 ml) (caution: vigorous CO2 evolution). More aqueous sodium hydrogen carbonate was added until the aqueous layer reached pH 8. The organic layer was removed and the aqueous layer extracted with DCM (5 mL). Combined organic layers were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to yield (E)-7-methoxy-3,4,5,6-tetrahydro-2H-azepine (1.2 g, 95%) as a clear oil. LCMS (+ESI) m/z 128.2 [M+H]+. 1H-NMR (CDCl3) δ 3.60 (s, 3H), 3.45 (m, 2H), 2.40 (m, 2H), 1.80 (m, 2H), 1.60-1.50 (m, 4H).

1. customThe reaction was quenched by the addition of saturated aqueous NaHCO3 (5 ml) (caution: vigorous CO2 evolution)
2. additionMore aqueous sodium hydrogen carbonate was added until the aqueous layer
3. customThe organic layer was removed
4. extractionthe aqueous layer extracted with DCM (5 mL)
5. dry with materialCombined organic layers were dried over anhydrous sodium sulfate
6. filtrationfiltered
7. customevaporated under reduced pressure

ORDレコード

ord-4262bba1d39f461f8e2b51334b7b7da5

出典データセット

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08835422B2