Hydrochloric Acid → HCID 68290960, compound

HRID 713129Notes

Reaction equation

HRID 713129 reaction equation
COC1C=CC(C[N:10]2[CH2:27][C:14]3([CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)[O:13][CH:12]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:11]2=[O:34])=CC=1.O.[ClH:36]>C(#N)C>[ClH:36].[C:28]1([CH:12]2[O:13][C:14]3([CH2:15][CH2:16][NH:17][CH2:18][CH2:19]3)[CH2:27][NH:10][C:11]2=[O:34])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 70872946Tert-butyl 10-[(4-methoxyphenyl)methyl]-9-oxo-8-phenyl-7-oxa-3,10-diazaspiro[5.5]undecane-3-carboxylate

Product 1

HCID 68290960HCID 68290960, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To tert-butyl 10-[(4-methoxyphenyl)methyl]-9-oxo-8-phenyl-7-oxa-3,10-diazaspiro[5.5]undecane-3-carboxylate (215 mg, 0.46 mmol) in acetonitrile (2.5 mL) was added water (2.5 mL) followed by the addition of ceric ammonium nitrate (500 mg, 0.91 mmol). The reaction mixture was stirred for 2 hours. After this time, a further aliquot of ceric ammonium nitrate (250 mg, 0.46 mmol) was added and the reaction mixture was stirred for an additional 45 minutes, it was then diluted with 1M aq. HCl, extracted with ethyl acetate (2×25 mL), dried over MgSO4 and concentrated in vacuo. The residue was dissolved in methanol (1 mL) and HCl (1 mL of 4 M in dioxane, 4.00 mmol) was added. The reaction mixture was stirred for 1 hour, then concentrated in vacuo to give 10-phenyl-11-oxa-3,8-diazaspiro[5.5]undecan-9-one hydrochloride salt (130 mg, 100%). ESI-MS m/z calc. 246.1. found 247.5 (M+1)+; Retention time: 0.46 minutes (3 min run).

Workup

  1. stirringthe reaction mixture was stirred for an additional 45 minutes
  2. extractionextracted with ethyl acetate (2×25 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in methanol (1 mL)
  6. stirringThe reaction mixture was stirred for 1 hour
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f54a20b6bda4f5ba6ebb2221d172cbc
Source dataset
uspto-grants-2015_11
Patent number
US09181273B2

Reaction notes

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