Tetrabutylammonium Fluoride → Tert-butyl 4-hydroxy-4-(3-hydroxyprop-1-yn-1-yl)piperidine-1-carboxylate

HRID 747005노트

반응식

HRID 747005 반응식
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH:19][C:20]1([C:33]#[C:34][CH2:35][O:36][Si](C)(C)C)[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1>O1CCCC1>[OH:19][C:20]1([C:33]#[C:34][CH2:35][OH:36])[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[CH2:22][CH2:21]1

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 219551731,1-Dimethylethyl 4-hydroxy-4-(3-trimethylsilyloxypropynyl)-1-piperidinecarboxylate

생성물 1

HCID 21955143Tert-butyl 4-hydroxy-4-(3-hydroxyprop-1-yn-1-yl)piperidine-1-carboxylate수율 88%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Tetrabutylammonium fluoride (1M in tetrahydrofuran, 80 ml, 80 mmol) was added to a solution of 1,1-dimethylethyl 4-hydroxy-4-(3-trimethylsilyloxypropynyl)-1-piperidinecarboxylate (from step (i) above; 24.4 g, 75 mmol) in tetrahydrofuran (300 ml) and the mixture was stirred at room temperature for 18 hours. The solvent was evaporated under reduced pressure and water (200 ml) was added. The mixture was extracted with ethyl acetate (2×200 ml) and the combined organic fractions were washed with water (2×200 ml) and brine (200 ml), dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as an orange oil (16.8 g, 88%).

후처리

  1. customThe solvent was evaporated under reduced pressure and water (200 ml)
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate (2×200 ml)
  4. washthe combined organic fractions were washed with water (2×200 ml) and brine (200 ml)
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-ecdc51dc4d87408d952d3f4cf6833f6a
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07393858B2

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