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

HRID 1474737
ノート
印刷プレビュー

反応式

HRID 1474737 の反応式
[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
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 89584039(6-{4-[(1R,2S)-2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)cyclopropyl]piperidin-1-yl}pyridin-3-yl)methanol

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 14798Sodium Hydroxide
溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-ddc48764503c4f98bc72851c1e05b6d5
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09018224B2

反応ノート

読み込み中…

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