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Tetrabutylammonium Fluoride → 4-{2-{Cyclopropylmethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amino}ethyl}phenol

HRID 1434154
ノート
印刷プレビュー

反応式

HRID 1434154 の反応式
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][N:17]([C:23]2[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:24]=2[CH:31]2[CH2:40][CH2:39][C:38]3[C:33](=[CH:34][CH:35]=[C:36]([O:41][CH3:42])[CH:37]=3)[CH2:32]2)[C:18]([CH:20]2[CH2:22][CH2:21]2)=O)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[Si](OC1C=CC(CCN(CC2CC2)C2C=C(OC)C=CC=2C2CCC3C(=CC=C(OC)C=3)C2)=CC=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[CH:20]1([CH2:18][N:17]([C:23]2[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:24]=2[CH:31]2[CH2:40][CH2:39][C:38]3[C:33](=[CH:34][CH:35]=[C:36]([O:41][CH3:42])[CH:37]=3)[CH2:32]2)[CH2:16][CH2:15][C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)[CH2:22][CH2:21]1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 3

HCID 2724141Tetrabutylammonium FluorideHCID 57933985Cyclopropanecarboxylic acid {2-[4-(tert-butyldimethylsilyloxy)phenyl]ethyl}[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amideHCID 66627570{2-[4-(Tert-butyldimethylsilyloxy)phenyl]ethyl}cyclopropylmethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine

生成物 1

HCID 230875484-{2-{Cyclopropylmethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amino}ethyl}phenol
収率 94.6%

実験手順

Synthesized from cyclopropanecarboxylic acid {2-[4-(tert-butyldimethylsilyloxy)phenyl]ethyl}[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amide (2.3 g) according to an analogous synthetic method to Example 337, to a filtrate of the resulting {2-[4-(tert-butyldimethylsilyloxy)phenyl]ethyl}cyclopropylmethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine was added tetrabutylammonium fluoride (1M solution in tetrahydrofuran) (4 ml), and the solution was stirred for 20 minutes at room temperature. The reaction solution was concentrated in vacuo, extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (1.7 g).

後処理

  1. concentrationThe reaction solution was concentrated in vacuo
  2. extractionextracted with ethyl acetate
  3. washsequentially washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

出典と根拠

ORDレコード
ord-e647ff47ed2040978fd8135dfac7dc43
出典データセット
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07612114B2

反応ノート

読み込み中…

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