Ethanol → tert-butyl 4-[(4-cyanopiperidin-1-yl)methyl]tetrahydro-2H-pyran-4-carboxylate

HRID 16578

Reaktionsgleichung

O=[C:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH2:4][CH2:3]1.C1(C)C=CC(S([CH2:31][N+:32]#[C-])(=O)=O)=CC=1.CCO.CC([O-])(C)C.[K+].C([O-])(O)=O.[Na+]>COCCOC>[C:31]([CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH2:4][CH2:3]1)#[N:32]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a stirred solution of tert-butyl 4-[(4-oxopiperidin-1-yl)methyl]tetrahydro-2H-pyran-4-carboxylate (8.77 g, 0.0295 mol, step 3) in 1,2-dimethoxyethane (250 mL) was added p-toluenesulfonylmethyl isocyanide (11.51 g, 0.0590 mol), EtOH (3.96 mL, 0.0678 mol) and t-BuOK (11.58 g, 0.1032 mol) at 0° C. The resulting mixture was stirred at 50° C. for 16 h. After cooling, the reaction mixture was poured into sat. NaHCO3 aq. (200 mL), and the mixture was extracted with CH2Cl2 (200 mL×3 times). The extracts were dried over Na2SO4 and concentrated. The residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (2:1) to give 5.76 g (63%) of the title compound as a yellow syrup.

Aufarbeitung

temperatureAfter cooling
extractionthe mixture was extracted with CH2Cl2 (200 mL×3 times)
dry with materialThe extracts were dried over Na2SO4
concentrationconcentrated
customThe residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (2:1)

Quellen und Nachweise

ORD-Eintrag: ord-62002d89563944d58f765513a967c8e1
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07737163B2

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