Reaktion #605339

ord-bcd76ef309754d07aad3c4b336cbdbb5

Reaktionsgleichung

COC(=O)/C=C/c1ccc2c(c1)C(=O)CC1(CCNCC1)O2
Intermediate 1
COC(=O)/C=C/c1ccc2c(c1)C(=O)CC1(CCNCC1)O2
(E)-3-{4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester
CC(C)(C)OC(=O)N1CCC2(CC1)Oc1ccc(Br)cc1C2=O
5-bromo-3-oxo-spiro[benzofuran-2(3H), 4′-piperidin]-1′-carboxylic acid tert-butyl ester
→
COC(=O)/C=C/c1ccc2c(c1)C(=O)C1(CCN(C(=O)OC(C)(C)C)CC1)O2
(E)-3-{1′-Tert-butoxycarbonyl-3-oxo-spiro[benzofuran-2(3H), 4′-piperidin]-5-yl}-acrylic acid methyl ester
COC(=O)/C=C/c1ccc2c(c1)C(=O)C1(CCNCC1)O2
desired compound
COC(=O)/C=C/c1ccc2c(c1)C(=O)C1(CCNCC1)O2
(E)-3-{3-oxo-spiro[benzofuran-2(3H), 4′-piperidin]-5-yl}-acrylic acid methyl ester

Edukte

COC(=O)/C=C/c1ccc2c(c1)C(=O)CC1(CCNCC1)O2
Intermediate 1
COC(=O)/C=C/c1ccc2c(c1)C(=O)CC1(CCNCC1)O2
(E)-3-{4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester
CC(C)(C)OC(=O)N1CCC2(CC1)Oc1ccc(Br)cc1C2=O
5-bromo-3-oxo-spiro[benzofuran-2(3H), 4′-piperidin]-1′-carboxylic acid tert-butyl ester

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigePurification by column chromatography (eluent hexane/AcOEt:80/20 to 70/30)

Vorschrift

(E)-3-{1′-Tert-butoxycarbonyl-3-oxo-spiro[benzofuran-2(3H), 4′-piperidin]-5-yl}-acrylic acid methyl ester was synthesized according to the procedure for preparation of Intermediate 1, Step B starting from 5-bromo-3-oxo-spiro[benzofuran-2(3H), 4′-piperidin]-1′-carboxylic acid tert-butyl ester. Purification by column chromatography (eluent hexane/AcOEt:80/20 to 70/30) furnished the desired compound (780 mg).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09115148B2uspto-grants-2015_08