Water → HCID 178485998、化合物

HRID 2057239ノート

反応式

HRID 2057239 の反応式
[CH2:1]([O:8][C:9](=[O:26])[N:10]([C@H:12]1[CH2:17][CH2:16][C@H:15]([O:18][Si](C(C)(C)C)(C)C)[CH2:14][CH2:13]1)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+:32](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[NH2:32][C:15]1([OH:18])[CH2:16][CH2:17][CH2:12][CH2:13][CH2:14]1.[CH2:1]([O:8][C:9](=[O:26])[N:10]([C@H:12]1[CH2:17][CH2:16][C@H:15]([OH:18])[CH2:14][CH2:13]1)[CH3:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 178486000HCID 178486000、化合物

生成物 2

HCID 147398371-Aminocyclohexan-1-olHCID 178485998HCID 178485998、化合物収率 180.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 3.1 g (8 mmol) trans-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-methyl-carbamic acid benzyl ester in 20 ml THF, 10.3 ml (1M, 10.3 mmol, 1.3 eq) Tetrabutylammonium fluoride in THF were added at 6° C. and the mixture was stirred at RT for 2 days. Water was added and the phases were separated and the inorganic phase was extracted with ether and EtOAc. The combined organic phases were washed with brine, dried over Na2SO4 and evaporated. Column chromatography on silica gel with a gradient EtOAc:hexane 1:4—EtOAc yielded 1.9 g 1.9 g (92%) trans-(4-Hydroxy-cyclohexyl)-methyl-carbamic acid benzyl ester as orange oil, MS: 263 (M).

後処理

  1. customthe phases were separated
  2. extractionthe inorganic phase was extracted with ether and EtOAc
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

出典と根拠

ORDレコード
ord-90a6aafb3492419dae7ffb6abba5ccd0
出典データセット
uspto-grants-2008_02
特許番号
US07335687B2

反応ノート

読み込み中…