1-[4-(2-(Azepan-1-yl)ethoxy)benzyl]-5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indole → Bazedoxifene

HRID 1862562ノート

反応式

HRID 1862562 の反応式
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:21][CH:20]=1)[C:13]([C:35]1[CH:40]=[CH:39][C:38]([O:41]CC3C=CC=CC=3)=[CH:37][CH:36]=1)=[C:12]2[CH3:49])C1C=CC=CC=1>C1COCC1.CCO>[N:28]1([CH2:27][CH2:26][O:25][C:22]2[CH:21]=[CH:20][C:19]([CH2:18][N:14]3[C:15]4[C:11](=[CH:10][C:9]([OH:8])=[CH:17][CH:16]=4)[C:12]([CH3:49])=[C:13]3[C:35]3[CH:36]=[CH:37][C:38]([OH:41])=[CH:39][CH:40]=3)=[CH:24][CH:23]=2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

参加物

3

反応物 1

HCID 98958311-[4-(2-(Azepan-1-yl)ethoxy)benzyl]-5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indole

生成物 1

HCID 154257Bazedoxifene

試薬・触媒・溶媒 1

HCID 21873804Tetrahydrofuran ethanol溶媒

実験手順

A solution consisting of indole 44 (17.5g, 26.9 mmol) in THF/EtOH (1:1) was hydrogenated under an atmosphere of H2 using 10% Pd/C as a catalyst. Chromatography on silica gel CH2Cl2/MeOH (gradient from 100/0 to 85/15) yields the desired product as 8.5 g of white foam along with 2.5 g of a fraction containing small impurities. Although the free base is the material used in the next step (bis-glucuronidation), for purposes of characterization and enhancing the compounds shelf life an acid addition salt may be made with HCl by dissolving the compound in MeOH and treating with 1.1 eq of a 2 N aq HCl solution. The compound slowly precipitates out as white crystals. Physical data listed below describes the HCl salt of indole 45:

出典と根拠

ORDレコード
ord-fa4dfd38c6944c3ca10afd6a3617661b
出典データセット
uspto-grants-2003_03
特許番号
US06537971B2

反応ノート

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