4-Nitrophenol → 1-(3-isopropyl-1,2,4-oxadiazol-5-yl)-4-{(1R,2S)-2-[2-(4-nitrophenoxy)ethyl]cyclopropyl}piperidine

HRID 1850736ノート

反応式

HRID 1850736 の反応式
[CH:1]([C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([C@H:15]3[CH2:17][C@H:16]3[CH2:18][CH2:19][OH:20])[CH2:11][CH2:10]2)[O:6][N:5]=1)([CH3:3])[CH3:2].[N+:21]([C:24]1[CH:29]=[CH:28][C:27](O)=[CH:26][CH:25]=1)([O-:23])=[O:22].C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CN(C=O)C>[CH:1]([C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([C@H:15]3[CH2:17][C@H:16]3[CH2:18][CH2:19][O:20][C:27]3[CH:28]=[CH:29][C:24]([N+:21]([O-:23])=[O:22])=[CH:25][CH:26]=3)[CH2:11][CH2:10]2)[O:6][N:5]=1)([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 9804-NitrophenolHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 708186512-((1S,2R)-2-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)cyclopropyl)ethanol

生成物 1

HCID 867111861-(3-isopropyl-1,2,4-oxadiazol-5-yl)-4-{(1R,2S)-2-[2-(4-nitrophenoxy)ethyl]cyclopropyl}piperidine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2-{(1S,2R)-2-[1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl]cyclopropyl}ethanol (367 mg, 0.943 mmol) in DMF (3 ml) at room temperature under nitrogen was added 4-nitrophenol (144 mg, 1.037 mmol), followed by cesium carbonate (614 mg, 1.886 mmol) and the resulting mixture stirred at room temperature overnight. Ethyl acetate (50 mL) was added and washed with water followed by brine. The organic layer was then dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure to afford the crude product which was used for the next reaction without further purification. LCMS: retention 1.24 min/2.0 minute run: (ESI) m/z 401 [M+H]+.

後処理

  1. washwashed with water
  2. dry with materialThe organic layer was then dried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-62fbe783d66646c3aad53dd5a5164be6
出典データセット
uspto-grants-2015_02
特許番号
US08957062B2

反応ノート

読み込み中…