Tetrabutylammonium Fluoride → 4-(2-Cyclopropylindol-1-yl)cyclohexanol

HRID 491033ノート

反応式

HRID 491033 の反応式
[Si]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[C:16]2[CH:24]2[CH2:26][CH2:25]2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH:24]1([C:16]2[N:15]([CH:12]3[CH2:13][CH2:14][CH:9]([OH:8])[CH2:10][CH2:11]3)[C:23]3[C:18]([CH:17]=2)=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:26][CH2:25]1

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 576757611-[4-(tert-Butyldimethylsilanyloxy)cyclohexyl]-2-cyclopropyl-1H-indole

生成物 1

HCID 576757584-(2-Cyclopropylindol-1-yl)cyclohexanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Crude 1-[4-(tert-butyldimethylsilanyloxy)cyclohexyl]-2-cyclopropyl-1H-indole from above (10.4 mmol) was dissolved in tetrahydrofuran (150 mL), and tetrabutylammonium fluoride (21 mL, 1 M in THF, 21 mmol) was added. After the reaction was stirred for 72 hours it was concentrated and the residue partitioned between ethyl acetate and water. The organic layer was dried (MgSO4), concentrated and purified by SiO2 chromatography (10-50% ethyl acetate/hexanes) to give two (cis/trans) isomers (355 mg of the more polar isomer, 681 mg of the less polar isomer) of the desired alcohol. LC-MS (C17H21NO calc'd 255) m/z 256 (M+H).

後処理

  1. concentrationwas concentrated
  2. customthe residue partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated
  5. custompurified by SiO2 chromatography (10-50% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-f88c4be0fd7143b2a56d7f9ba8358306
出典データセット
uspto-grants-2009_05
特許番号
US07528262B2

反応ノート

読み込み中…