Reaktionsgleichung
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].[C:8]([O:12][C:13]([N:15]1[CH2:18][C:17](=O)[CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].C(OC)(OC)OC.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C>CC(O)=O.ClCCCl>[C:8]([O:12][C:13]([N:15]1[CH2:18][CH:17]([N:4]2[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]2)[CH2:16]1)=[O:14])([CH3:11])([CH3:9])[CH3:10]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A mixture of piperazin-2-one (1.52 g, 15.1 mmol), 3-oxoazetidine-1-carboxylic acid tert-butyl ester (2.0 g, 11.6 mmol) and trimethyl orthoformate (12.8 mL, 12.4 g, 117 mmol) in AcOH (0.7 mL) and DCE (50 mL) was stirred for 5 h before the addition of triacetoxyborohydride (4.9 g, 23.2 mmol). The resulting mixture was stirred for 16 h then partitioned between DCM and H2O. The organic layer was dried (Na2SO4) and concentrated in vacuo. The resulting oil was purified by column chromatography (Si—PCC, MeOH:DCM, 0-10%) affording the title compound as a foam (827 mg, 28%). 1H NMR (CDCl3, 300 MHz): δ 6.24 (s, 1H); 3.97 (dd, J=8.9, 7.1 Hz, 2H); 3.82 (dd, J=5.2, 2.2 Hz, 2H); 3.40 (td, J=5.2, 2.2 Hz, 2H); 3.24-3.15 (m, 1H); 3.07 (s, 2H); 2.60 (t, J=5.4 Hz, 2H); 1.44 (s, 9H).
Aufarbeitung
- customthen partitioned between DCM and H2O
- dry with materialThe organic layer was dried (Na2SO4)
- concentrationconcentrated in vacuo
- customThe resulting oil was purified by column chromatography (Si—PCC, MeOH:DCM, 0-10%)
Quellen und Nachweise
- ORD-Eintrag
- ord-2b5ab7baedc645739cbee2dbd01aaf10
- Quelldatensatz
- uspto-grants-2012_05
- Patentnummer
- US08173650B2
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