Hydrochloric Acid → 8-Azabicyclo(3.2.1)octan-3-one

HRID 630329Notes

Reaction equation

HRID 630329 reaction equation
CC(OC([N:8]1[C@@H:12]2[CH2:13][C:14]([CH2:16][C@H:9]1[CH2:10][CH2:11]2)=[O:15])=O)(C)C.Cl.O1CCOCC1>ClCCl>[CH:9]12[NH:8][CH:12]([CH2:11][CH2:10]1)[CH2:13][C:14](=[O:15])[CH2:16]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 688612tert-butyl (1R,5S)-3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate

Product 1

HCID 4344538-Azabicyclo(3.2.1)octan-3-oneYield 128.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-Boc nortropinone (0.73 g, 3.24 mmol) in a minimal amount of dichloromethane (1 mL) was treated with a solution of 4 M hydrochloric acid in dioxane (3.2 mL, 12.8 mmol). After stirring for 2.5 days, the reaction was complete by TLC analysis. Solvent was removed under reduced pressure to give 0.52 g of 8-azabicyclo[3.2.1]octan-3-one.

Workup

  1. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-24d9a5ac72d848cfaefda865ca8509e2
Source dataset
uspto-grants-2016_04
Patent number
US09315509B2

Reaction notes

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