Benzylamine → Diethyl 1-benzylazetidine-3,3-dicarboxylate
Reaktionsgleichung
O[CH2:2][C:3]([CH2:14]O)([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].O(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.CCN(C(C)C)C(C)C.[CH2:40]([NH2:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>CC#N.[Cl-].[Na+].O.CC(=O)OCC>[CH2:40]([N:47]1[CH2:2][C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:14]1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1Komponenten
8
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 70 °C
Versuchsvorschrift
To a solution of diethyl 2,2-bis(hydroxymethyl)malonate (4.4 g, 20 mmol) in CH3CN (50 mL) was added Tf2O (7.1 mL, 11.85 g, 42 mmol) at −20° C., followed by two batches of DIEA (6.45 g, 50 mmol). After 0.5 hr, benzylamine (3.21 g, 35 mmol) was added at −20° C. The mixture was stirred at 70° C. for 2 hr. 100 mL of EA and 100 mL of brine were added. Organic layers were dried over Na2SO4. Purified by chromatography column on silica gel eluting with PE/EA to afford 4.8 g (82%) of diethyl 1-benzylazetidine-3,3-dicarboxylate as a yellow oil. 1H NMR (400 MHz, DMSO-d6) δ 7.29-7.34 (m, 2H), 7.22-7.27 (m, 3H), 4.17 (q, J=7.2 Hz, 4H), 3.56 (s, 2H), 3.51 (s, 4H), 2.39 (s, 3H) and 1.17 (t, J=7.2 Hz, 6H).
Aufarbeitung
- dry with materialOrganic layers were dried over Na2SO4
- customPurified by chromatography column on silica gel eluting with PE/EA
Quellen und Nachweise
- ORD-Eintrag
- ord-5299a1e5b7624e7e88a2647d7a20f13e
- Quelldatensatz
- uspto-grants-2016_09
- Patentnummer
- US09447106B2
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