Reaktionsgleichung
[OH:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl>[CH3:17][S:18]([O:1][CH2:2][CH2:3][CH:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9]1)(=[O:20])=[O:19]Komponenten
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
The reaction was prepared in 2 batches, with both batches purified together. The amounts of reactants and product reflect the sum of both batches. To 1,1-dimethylethyl 4-(2-hydroxyethyl)-1-piperidinecarboxylate (172 g, 750 mmol) in DCM (4 L) was added TEA (304 g, 1.50 mol). The mixture was cooled 0° C. and methanesulfonyl chloride (190 g, 827 mmol) was added dropwise. The reaction mixture was stirred at rt for 2 h. The reaction was determined to be complete by TLC. The reaction was diluted with DCM and washed with saturated Na2CO3 and the aqueous layer was separated. The organic layer was dried (Na2SO4), and rotovapped down to provide the title compound of Step B (280 g, 911 mmol, 61%). 1H NMR (400 MHz, CDCl3) δ 0.95-1.15 (m, 2H), 1.38 (s, 9H), 1.47-1.68 (m, 5H), 2.53-2.70 (m, 2H), 2.94 (s, 3H), 3.95-4.10 (m, 2H), 4.21 (t, J=8.8 Hz, 2H).
Aufarbeitung
- customThe reaction was prepared in 2 batches, with both batches
- custompurified together
- washwashed with saturated Na2CO3
- customthe aqueous layer was separated
- dry with materialThe organic layer was dried (Na2SO4)
Quellen und Nachweise
- ORD-Eintrag
- ord-691f670c6320449195fd7d685f71ea6f
- Quelldatensatz
- uspto-grants-2012_01
- Patentnummer
- US08093239B2
Verknüpfte Notizen
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