4-Methylphenethyl bromide → (E)-3-{1'-[2-(4-methyl-phenyl)-ethyl]-4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid methyl ester

HRID 2046751Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2046751
[CH3:1][O:2][C:3](=[O:29])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:25](=[CH:26][CH:27]=1)[O:24][C:11]1([CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:28].Br[CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=1>>[CH3:1][O:2][C:3](=[O:29])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:25](=[CH:26][CH:27]=1)[O:24][C:11]1([CH2:12][CH2:13][N:14]([CH2:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=3)[CH2:15][CH2:16]1)[CH2:10][C:9]2=[O:28]

Komponenten

3

Edukt 2

HCID 5706804-Methylphenethyl bromideHCID 52952087(E)-3-{1'-tert-butoxycarbonyl-4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid methyl ester2×

Produkt 1

HCID 66932181(E)-3-{1'-[2-(4-methyl-phenyl)-ethyl]-4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid methyl esterAusbeute 89,7 %

Versuchsvorschrift

(E)-3-{4-Oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (253 mg, 0.749 mmol, Intermediate 1, hydrochloride salt) was alkylated using 1-(2-bromo-ethyl)-4-methyl-benzene (0.23 ml, 1.5 mmol) as described in Example 56, Step A, giving (E)-3-{1′-[2-(4-methyl-phenyl)-ethyl]-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (282 mg) as a light brown solid.

Quellen und Nachweise

ORD-Eintrag
ord-ac770a4c66e04a0f86816fc195775c5d
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592444B2

Notizen zur Reaktion

Wird geladen…