Hydrochloric Acid → HCID 89649235, compound

HRID 2207672Notes

Reaction equation

HRID 2207672 reaction equation
Cl.O1CCOCC1.[O:8]=[C:9]1[NH:40][CH2:39][CH2:38][C@@:10]21[N:14](C(OC(C)(C)C)=O)[C@@H:13]([C:22]1[CH:27]=[C:26]([C:28]3[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=3)[CH:25]=[CH:24][N:23]=1)[CH2:12][CH2:11]2>>[F:37][C:34]([F:35])([F:36])[C:31]1[CH:32]=[CH:33][C:28]([C:26]2[CH:25]=[CH:24][N:23]=[C:22]([C@H:13]3[CH2:12][CH2:11][C@@:10]4([CH2:38][CH2:39][NH:40][C:9]4=[O:8])[NH:14]3)[CH:27]=2)=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131735928HCID 131735928, compound

Product 1

HCID 89649235HCID 89649235, compound

Procedure

4 M HCl in dioxane (3 mL, 12 mmol) was added to the tert-butyl (2R,5S)-6-oxo-2-[4-[4-(trifluoromethyl)phenyl]-2-pyridyl]-1,7-diazaspiro[4.4]nonane-1-carboxylate and the reaction mixture stirred for 16 hours. The mixture was concentrated at reduced pressure and then re-dissolved in methanol. The solution was applied to an SCX column which was eluted with methanol, followed by 0.5 M ammonia in methanol. Basic product containing fractions were combined and concentrated to give (2R,5S)-2-[4-[4-(trifluoromethyl)phenyl]-2-pyridyl]-1,7-diazaspiro[4.4]nonan-6-one as a colourless solid (36 mg);

Workup

  1. concentrationThe mixture was concentrated at reduced pressure
  2. dissolutionre-dissolved in methanol
  3. washwas eluted with methanol
  4. additionBasic product containing fractions
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8d72871ffc504422990e9c081d843eb5
Source dataset
uspto-grants-2016_06
Patent number
US09376436B2

Reaction notes

Loading…