Formaldehyde → HCID 68338070, Verbindung
Reaktionsgleichung
[O:1]=[C:2]1[C:11]2([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH2:10][C:9]2[C:4](=[N:5][CH:6]=[C:7](/[CH:17]=[CH:18]/[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=2)[NH:3]1.[C:24](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O>ClCCCl>[CH3:24][N:14]1[CH2:13][CH2:12][C:11]2([CH2:10][C:9]3[C:4](=[N:5][CH:6]=[C:7](/[CH:17]=[CH:18]/[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=3)[NH:3][C:2]2=[O:1])[CH2:16][CH2:15]1Komponenten
5
Reaktionsbedingungen
- Temperatur
- 70 °C
Versuchsvorschrift
To a suspension of (E)-ethyl 3-(2-oxo-2,4-dihydro-1H-spiro[[1,8]naphthyridine-3,4′-piperidine]-6-yl)acrylate (99.8 mg, 0.316 mmol) in 1,2-dichloroethane (5 mL) were added sodium triacetoxyborohydride (139 mg, 0.656 mmol) and paraformaldehyde (21 mg, 0.699 mmol). The reaction mixture was heated to 70° C. for 5 h. After cooling to room temperature, the reaction mixture was partitioned between DCM (25 mL) and water (25 mL). The aqueous layer was separated and extracted with DCM (2×20 mL). The combined organic phases were washed with saturated NaHCO3 (3×25 mL) and brine (25 mL), dried over sodium sulfate and concentrated. The crude product was used directly in the next step.
Aufarbeitung
- temperatureAfter cooling to room temperature
- customthe reaction mixture was partitioned between DCM (25 mL) and water (25 mL)
- customThe aqueous layer was separated
- extractionextracted with DCM (2×20 mL)
- washThe combined organic phases were washed with saturated NaHCO3 (3×25 mL) and brine (25 mL)
- dry with materialdried over sodium sulfate
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-f3aff27617b94a17bea5d4561c1033f3
- Quelldatensatz
- uspto-grants-2016_04
- Patentnummer
- US09321769B2
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