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

HRID 564572

Reaction equation

HRID 564572 reaction equation
[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

Participants

4

Reactant 2

HCID 79038Npc164516HCID 10979718Diethyl 3-Bromobenzylphosphonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-730db2631bad47f1b4457f1dd7b7ad5e
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Linked notes

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