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

HRID 564572

반응식

HRID 564572 반응식
[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

참가 물질

4

반응물 2

HCID 79038Npc164516HCID 10979718Diethyl 3-Bromobenzylphosphonate

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-730db2631bad47f1b4457f1dd7b7ad5e
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067408B2

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