Potassium Carbonate → HCID 58550791, compound

HRID 2204136Notes

Reaction equation

HRID 2204136 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[C:13]1([OH:26])[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:16]1([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18][C:13]2([C:9]3=[N:10][CH:11]=[CH:12][N:8]3[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[O:26]2)[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 58551780HCID 58551780, compound

Product 1

HCID 58550791HCID 58550791, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl 4-[1-(2-fluorophenyl)imidazol-2-yl]-4-hydroxy-piperidine-1-carboxylate (294 mg, 0.81 mmol) and K2CO3 (337 mg, 2.44 mmol) were heated at 110° C. for 16 h in DMF (5 mL). The solvent was evaporated and the resulting material was partitioned between dichloromethane and water. The organics were separated and washed with brine, dried over sodium sulfate and evaporated. The crude material was purified by column chromatography (0-50% ethyl acetate in hexanes) to give tert-butyl spiro[imidazo[2,1-c][1,4]benzoxazine-4,4′-piperidine]-1′-carboxylate (139 mg, 50%). ESI-MS m/z calc. 341.2, found 342.3 (M+1)+. Retention time 1.31 minutes (3 min run).

Workup

  1. customThe solvent was evaporated
  2. customthe resulting material was partitioned between dichloromethane and water
  3. customThe organics were separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe crude material was purified by column chromatography (0-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-3cf54bcb61514d96ba194d57b072abd5
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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