Hydrochloric Acid → HCID 117697851, compound

HRID 1778517Notes

Reaction equation

HRID 1778517 reaction equation
[O:1]=[C:2]1[CH2:9][CH:8]2[N:10](C(OC(C)(C)C)=O)[CH:4]([CH2:5][O:6][CH2:7]2)[CH2:3]1.C(O[CH:23](N(C)C)[N:24](C)C)(C)(C)C.NO.Cl.Cl>O1CCOCC1>[CH:8]12[NH:10][CH:4]([CH2:5][O:6][CH2:7]1)[CH2:3][C:2]1[O:1][N:24]=[CH:23][C:9]2=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 443297Hydroxyamine hydrochlorideHCID 185070529-Boc-7-oxa-9-azabicyclo[3.3.1]nonan-3-one

Product 1

HCID 117697851HCID 117697851, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 7-oxo-3-oxa-9-azabicyclo[3.3.1]nonane-9-carboxylate (482 mg, 2 mmol) and tert-butoxy-N,N,N′,N′-tetra-methyl-methanediamine (522 mg) in dioxane (10 mL) was stirred at 60° C. for 16 h. The solvent was removed in vacuo, and the residue was dissolved in EtOH (10 mL). To it NH2OH.HCl (462 mg, 3 mmol) was added. After stirring at room temperature for 2 h, 12 N HCl (1 mL) was added and refluxed for 2 h. The reaction mixture was concentrated to give 5,10-Dioxa-4,12-diaza-tricyclo[6.3.1.0*2,6*]dodeca-2(6),3-diene 105a as an oil (yield 100%), which was used without further purification. MS: calc'd (MH+) 167, measured (MH+) 167.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in EtOH (10 mL)
  3. temperaturerefluxed for 2 h
  4. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-018f6cb6c47b40129be8594c05344b1e
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

Loading…