Sodium Bicarbonate → (S)-tert-butyl 4-((S)-1-phenylethylamino)-3,4-dihydro-2H-spiro[naphthalene-1,4'-piperidine]-1'-carboxylate
Reaktionsgleichung
[BH4-].[Na+].[C:3]1([C@@H:9]([N:11]=[C:12]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:15]3([CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)[CH2:14][CH2:13]2)[CH3:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O-])(O)=O.[Na+]>CO>[C:3]1([C@@H:9]([NH:11][C@@H:12]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:15]3([CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:26])([CH3:27])[CH3:25])=[O:22])[CH2:19][CH2:20]3)[CH2:14][CH2:13]2)[CH3:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
At −78° C., NaBH4 (760 mg, 20 mmol) was added to a solution of the imine (B1) (7.82 g, 20 mmol) in methanol (100 ml). The reaction mixture was allowed to warm to 0° C. over 2-3 hours then treated with saturated NaHCO3 (ca. 100 ml), concentrated under reduced pressure at <30° C. to remove the solvent. The residue was extracted with ethyl acetate. The organic phase was washed with water, dried over Na2SO4 and concentrated to give (S)-tert-butyl 4-((S)-1-phenylethylamino)-3,4-dihydro-2H-spiro[naphthalene-1,4′-piperidine]-1′-carboxylate (B2) as a solid. LC-MS: m/e=421.32 (M+H). Rt=2.20 min.
Aufarbeitung
- concentrationconcentrated under reduced pressure at <30° C.
- customto remove the solvent
- extractionThe residue was extracted with ethyl acetate
- washThe organic phase was washed with water
- dry with materialdried over Na2SO4
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-91a7ea236d074f6cb3988f9c47eb4779
- Quelldatensatz
- uspto-grants-2012_11
- Patentnummer
- US08304423B2
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