Npc164516 → 3-[(3-Bromophenyl)methylidene]-8-methyl-8-azabicyclo[3.2.1]octane

HRID 564572

反応式

HRID 564572 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8]P(=O)(OCC)OCC)[CH:5]=[CH:6][CH:7]=1.[CH3:17][N:18]1[CH:23]2[CH2:24][CH2:25][CH:19]1[CH2:20][C:21](=O)[CH2:22]2>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:21]2[CH2:22][CH:23]3[N:18]([CH3:17])[CH:19]([CH2:25][CH2:24]3)[CH2:20]2)[CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 79038Npc164516HCID 10979718Diethyl 3-Bromobenzylphosphonate

生成物 1

HCID 578134113-[(3-Bromophenyl)methylidene]-8-methyl-8-azabicyclo[3.2.1]octane収率 85%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of diethyl [(3-bromophenyl)methyl]phosphonate (3.07 g, 10 mmol) in THF (20 mL) was added 8-methyl-8-azabicyclo[3.2.1]octan-3-one (1.67 g, 12 mmol) then KOBu-t (1.234 g, 11 mmol). The reaction mixture was stirred at room temperature for 5 h before it was quenched with NH4Cl (5 mL, saturated aqueous). The organic layer of the reaction mixture was separated and the aqueous layer was extracted with DCM (5 mL). The combined organic layers were loaded onto a Combiflash Redisep silica gel column (40 g) and purified by Combiflash chromatograph to afford 2.48 g (85%) of the title compound. LC-MS m/z 292 (M+H)+.

後処理

  1. customwas quenched with NH4Cl (5 mL, saturated aqueous)
  2. customThe organic layer of the reaction mixture was separated
  3. extractionthe aqueous layer was extracted with DCM (5 mL)
  4. custompurified by Combiflash chromatograph

出典と根拠

ORDレコード
ord-730db2631bad47f1b4457f1dd7b7ad5e
出典データセット
uspto-grants-2011_11
特許番号
US08067408B2

関連ノート

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