Ammonia → 6-{2-{(2-Fluoroethyl)[3-fluoro-4-(2-piperidin-1-ylethoxy)benzyl]amino}-4-hydroxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1433976ノート

反応式

HRID 1433976 の反応式
[Si]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:36]2[CH2:45][CH2:44][C:43]3[C:38](=[CH:39][CH:40]=[C:41]([O:46][Si](C(C)(C)C)(C)C)[CH:42]=3)[CH2:37]2)=[C:13]([N:15]([CH2:33][CH2:34][F:35])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[C:19]([F:32])[CH:18]=2)[CH:14]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl.CO.N>O1CCCC1>[F:35][CH2:34][CH2:33][N:15]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]2[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)=[C:19]([F:32])[CH:18]=1)[C:13]1[CH:14]=[C:9]([OH:8])[CH:10]=[CH:11][C:12]=1[CH:36]1[CH2:45][CH2:44][C:43]2[CH:42]=[C:41]([OH:46])[CH:40]=[CH:39][C:38]=2[CH2:37]1

参加物

6

反応物 4

HCID 222AmmoniaHCID 2724141Tetrabutylammonium FluorideHCID 21893726Hydrochloride methanolHCID 57933781{5-(tert-Butyldimethylsilyloxy)-2-[6-(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalen-2-yl]phenyl}(2-fluoroethyl)[3-fluoro-4-(2-piperidin-1-ylethoxy)benzyl]amine

生成物 1

HCID 579340976-{2-{(2-Fluoroethyl)[3-fluoro-4-(2-piperidin-1-ylethoxy)benzyl]amino}-4-hydroxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol収率 99.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

solution of {5-(tert-butyldimethylsilyloxy)-2-[6-(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalen-2-yl]phenyl}(2-fluoroethyl)[3-fluoro-4-(2-piperidin-1-ylethoxy)benzyl]amine (200 mg) in tetrahydrofuran (10 ml) were sequentially added tetrabutylammonium fluoride (1.0 M solution in tetrahydrofuran) (1 ml) and hydrochloric acid-methanol solution (1 ml) on an ice bath, and the solution was stirred for 8 hours at 50° C. The reaction solution was alkalinized by adding aqueous ammonia, the solution was extracted with ethyl acetate, then washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate-methanol system) to provide the title compound (140 mg).

後処理

  1. extractionthe solution was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was purified by NH silica gel column chromatography (hexane-ethyl acetate-methanol system)

出典と根拠

ORDレコード
ord-bbb1f2e096354926af264662d3e6870b
出典データセット
uspto-grants-2009_11
特許番号
US07612114B2

反応ノート

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