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Tetrabutylammonium Fluoride → 2-[(1S,2R)-2-{1-[5-(methoxymethyl)pyridin-2-yl]piperidin-4-yl}cyclopropyl]ethanol

HRID 1474737
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HRID 1474737 반응식
[Si]([O:8][CH2:9][CH2:10][C@@H:11]1[CH2:13][C@@H:12]1[CH:14]1[CH2:19][CH2:18][N:17]([C:20]2[N:25]=[CH:24][C:23]([CH2:26][OH:27])=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)(C(C)(C)C)(C)C.[CH3:28]CCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.[OH-].[Na+]>[CH3:28][O:27][CH2:26][C:23]1[CH:22]=[CH:21][C:20]([N:17]2[CH2:16][CH2:15][CH:14]([C@H:12]3[CH2:13][C@H:11]3[CH2:10][CH2:9][OH:8])[CH2:19][CH2:18]2)=[N:25][CH:24]=1
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참가 물질

5

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 89584039(6-{4-[(1R,2S)-2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)cyclopropyl]piperidin-1-yl}pyridin-3-yl)methanol

생성물 1

HCID 895841062-[(1S,2R)-2-{1-[5-(methoxymethyl)pyridin-2-yl]piperidin-4-yl}cyclopropyl]ethanol

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 14798Sodium Hydroxide
용매

실험 절차

The (6-{4-[(1R,2S)-2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)cyclopropyl]piperidin-1-yl}pyridin-3-yl)methanol (2.471 ml, 0.494 mmol) was dissolved in THF (1.236 ml) and TBAF (0.741 ml, 0.741 mmol) added. The mixture was stirred at room temperature for 1 hour. The mixture was diluted with 1N NaOH (50 ml), extracted with EtOAc (3×30 ml), the organic fractions combined, washed with brine, dried over sodium sulfate, filtered and the volatiles removed in vacuo. The residue was purified by column chromatography on silica gel, Biotage 25 g, using a gradient eluant of 0-100% EtOAc/hexanes to afford the title compound. LC/MS (m/z): 291 (M+H)+.

후처리

  1. extractionextracted with EtOAc (3×30 ml)
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe volatiles removed in vacuo
  6. customThe residue was purified by column chromatography on silica gel, Biotage 25 g

출처 및 근거

ORD 기록
ord-ddc48764503c4f98bc72851c1e05b6d5
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09018224B2

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