tert-Butyl 5-bromo-3-oxo-3H-spiro[benzofuran-2,4'-piperidine]-1'-carboxylate → (E)-3-{1'-Tert-butoxycarbonyl-3-oxo-spiro[benzofuran-2(3H), 4'-piperidin]-5-yl}-acrylic acid methyl ester

HRID 518157Notes

Reaction equation

HRID 518157 reaction equation
[CH3:1][O:2][C:3](=[O:22])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:18](=[CH:19][CH:20]=1)[O:17][C:11]1([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)C[C:9]2=[O:21].[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][C:33]2([C:39](=[O:40])[C:38]3[CH:41]=[C:42](Br)[CH:43]=[CH:44][C:37]=3[O:36]2)[CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>>[CH3:1][O:2][C:3](=[O:22])/[CH:4]=[CH:5]/[C:42]1[CH:43]=[CH:44][C:37]2[O:36][C:33]3([CH2:34][CH2:35][N:30]([C:28]([O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:29])[CH2:31][CH2:32]3)[C:39](=[O:40])[C:38]=2[CH:41]=1.[CH3:1][O:2][C:3](=[O:22])/[CH:4]=[CH:5]/[C:6]1[CH:20]=[CH:19][C:18]2[O:17][C:11]3([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:9](=[O:21])[C:8]=2[CH:7]=1

Participants

4

Reactant 2

HCID 11474505tert-Butyl 5-bromo-3-oxo-3H-spiro[benzofuran-2,4'-piperidine]-1'-carboxylateHCID 52952093(E)-3-{4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid methyl ester

Product 2

HCID 11406566(E)-3-{1'-Tert-butoxycarbonyl-3-oxo-spiro[benzofuran-2(3H), 4'-piperidin]-5-yl}-acrylic acid methyl esterHCID 52952195(E)-3-{3-oxo-spiro[benzofuran-2(3H), 4'-piperidin]-5-yl}-acrylic acid methyl ester

Procedure

(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).

Workup

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

Sources & evidence

ORD record
ord-bcd76ef309754d07aad3c4b336cbdbb5
Source dataset
uspto-grants-2015_08
Patent number
US09115148B2

Reaction notes

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