Reaktionsgleichung
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([CH2:16][C:15](=[O:17])[C:14]3[C:9](=[CH:10][CH:11]=[C:12](Br)[CH:13]=3)[O:8]2)[CH2:4][CH2:3]1.COC(=O)/C=C/C1C=C2C(=CC=1)OC1(CCN(C(OC(C)(C)C)=O)CC1)CC2=O.[C:48]([O:52][C:53](=[O:56])[CH:54]=[CH2:55])([CH3:51])([CH3:50])[CH3:49]>>[C:48]([O:52][C:53](=[O:56])/[CH:54]=[CH:55]/[C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[O:8][C:5]1([CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1)[CH2:16][C:15]2=[O:17])([CH3:51])([CH3:50])[CH3:49]Komponenten
Edukt 3
Produkt 1
Versuchsvorschrift
(E)-3-{1′-Methyl-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid tert-butyl ester was synthesized starting from 1′-methyl-6-bromo-spiro[chromane-2,4′-piperidine]-4-one (1.62 g, 5.22 mmol) according to the procedure for preparation of Intermediate 1, Step B, using tert-butylacrylate, giving a yellow solid (1.45 g). The resulting product was dissolved in a 20% TFA/DCM mixture (25 ml) and stirred at RT. After 16 h, the solvent was evaporated and the residue was partitioned between DCM and a saturated NaHCO3 solution. Then the aqueous phase was acidified with a 6 M solution of HCl and evaporated. The residue was suspended in a 9:1 DCM/MeOH mixture (70 ml) and the insoluble salts were filtered off. The solvent was dried over Na2SO4 and evaporated, giving (E)-3-{1′-methyl-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid (890 mg) as a yellow solid.
Quellen und Nachweise
- ORD-Eintrag
- ord-9ee9a0b7de7540d18c66ad71646b3ca1
- Quelldatensatz
- uspto-grants-2015_08
- Patentnummer
- US09115148B2
Verknüpfte Notizen
Wird geladen…