[Methoxy(tetrahydro-4H-pyran-4-ylidene)methoxy](trimethyl)silane → Methyl 4-[(4-{[(tert-butoxycarbonyl)amino]methyl}piperidin-1-yl)methyl]tetrahydro-2H-pyran-4-carboxylate

To a stirred solution of tert-butyl {[1-(ethoxymethyl)piperidin-4-yl]methyl}carbamate (4 g, 14 mmol, step 1 of Example 8) and [methoxy(tetrahydro-4H-pyran-4-ylidene)methoxy](trimethyl)silane (2.9 g, 13 mmol, step 2 of Example 8) in CH2Cl2 (30 mL) was added dropwise trimethylsilyl trifluoromethanesulfonate (0.24 mL, 1.3 mmol) at 0° C., and the resulting mixture was stirred at room temperature for 12 h. The reaction mixture was quenched with saturated aqueous sodium bicarbonate (150 mL), extracted with CH2Cl2 (30 mL×2), and the combined organic layer was dried over sodium sulfate and filtered. Removal of the solvent gave a residue, which was chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1:1) to give 6.3 g (64%) of the title compound as clear colorless oil.

1. customThe reaction mixture was quenched with saturated aqueous sodium bicarbonate (150 mL)
2. extractionextracted with CH2Cl2 (30 mL×2)
3. dry with materialthe combined organic layer was dried over sodium sulfate
4. filtrationfiltered
5. customRemoval of the solvent
6. customgave a residue, which
7. customwas chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1:1)

ORD 기록

ord-e3129407928e426e84ac3271b4a361e4

출처 데이터셋

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07589109B2