Pyridine → 8-Azabicyclo[3.2.1]octane-8-carbonyl chloride

HRID 2282665Notes

Reaction equation

HRID 2282665 reaction equation
[CH:1]12[NH:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3][CH2:2]2.N1C=CC=CC=1.[Cl:15][C:16](Cl)([O:18]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH:5]12[N:8]([C:16]([Cl:15])=[O:18])[CH:1]([CH2:7][CH2:6]1)[CH2:2][CH2:3][CH2:4]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 1360978-Azabicyclo(3.2.1)octane

Product 1

HCID 122475358-Azabicyclo[3.2.1]octane-8-carbonyl chlorideYield 70.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (10° C.) solution 8-aza-bicyclo[3.2.1]octane (295 mg, 2.00 mmol) and pyridine (486 μL, 6.02 mmol) in DCM (10 mL) was added triphosgene (595 mg, 2.00 mmol) portionwise. The reaction was allowed to reach room temperature and stirred overnight. The mixture was quenched with HCl (1M aqueous, 10 mL) and stirred for 30 min. The aqueous phase was extracted with DCM (×3) and the combined organic layers were washed with HCl (1M aqueous), brine, dried (MgSO4) and concentrated in vacuo, to give the title compound (244 mg, 70%). 1H NMR (400 MHz, CDCl3): 1.46-1.70 (4H, m), 1.72-1.92 (5H, m), 2.04-2.11 (2H, m), 4.39-4.44 (2H, m).

Workup

  1. customto reach room temperature
  2. customThe mixture was quenched with HCl (1M aqueous, 10 mL)
  3. stirringstirred for 30 min
  4. extractionThe aqueous phase was extracted with DCM (×3)
  5. washthe combined organic layers were washed with HCl (1M aqueous), brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-875c0513f04a44c59d945a8dbdf33141
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

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