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Tetrabutylammonium Fluoride → 2-[2-(4-Methoxycarbonylmethylphenoxy)-1(R)-methylethyl]amino-1 (R)-phenylethanol

HRID 1901172
ノート
印刷プレビュー

反応式

HRID 1901172 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][O:20][C:21]([CH2:23][C:24]1[CH:50]=[CH:49][C:27]([O:28][CH2:29][C@H:30]([NH:32][CH2:33][C@H:34]([O:41][Si](C(C)(C)C)(C)C)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH3:31])=[CH:26][CH:25]=1)=[O:22]>O1CCCC1.O>[CH3:19][O:20][C:21]([CH2:23][C:24]1[CH:50]=[CH:49][C:27]([O:28][CH2:29][C@H:30]([NH:32][CH2:33][C@@H:34]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[OH:41])[CH3:31])=[CH:26][CH:25]=1)=[O:22]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 22867085N-[2-(4-methoxycarbonylmethylphenoxy)-1(R)-methylethyl]-2(R)-t-butyldimethylsilyloxy-2-phenylethanamine

生成物 1

HCID 228731272-[2-(4-Methoxycarbonylmethylphenoxy)-1(R)-methylethyl]amino-1 (R)-phenylethanol収率 60.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028
Tetrahydrofuran
溶媒

実験手順

870 mg of tetrabutylammonium fluoride were added to a solution of 510 mg of N-[2-(4-methoxycarbonylmethylphenoxy)-1(R)-methylethyl]-2(R)-t-butyldimethylsilyloxy-2-phenylethanamine (prepared as described in Preparation 29) in 15 ml of tetrahydrofuran, and the resulting mixture was stirred at room temperature for 2 hours. At the end of this time, the reaction mixture was diluted with water, and the aqueous mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and then the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using ethyl acetate as the eluent, to give 0.23 g of the title compound as crystals, melting at 69°-70° C.

後処理

  1. extractionthe aqueous mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. customthe solvent was removed by distillation under reduced pressure
  4. customThe resulting residue was purified by column chromatography through silica gel

出典と根拠

ORDレコード
ord-7d455146396f497b99a42408951d6218
出典データセット
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05576340

反応ノート

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