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

HRID 2264697ノート

反応式

HRID 2264697 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-108342b19c3c4e3298752719744417f7
出典データセット
uspto-grants-2010_12
特許番号
US07855224B2

反応ノート

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