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

HRID 1901172
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HRID 1901172 반응식
[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]
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참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028
Tetrahydrofuran
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7d455146396f497b99a42408951d6218
출처 데이터셋
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05576340

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