Trifluoroacetic acid → HCID 58551585, compound

HRID 1907978Notes

Reaction equation

HRID 1907978 reaction equation
FC(F)(F)C(O)=O.[OH:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=1[N:19]1[CH:23]=[CH:22][CH:21]=[CH:20]1)[C:12]([O:14][CH3:15])=[O:13].O=[C:25]1[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]1>ClCCl>[N:28]1([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:29][CH2:30][C:25]2([O:8][C:9]3[CH:10]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[CH:16]=[CH:17][C:18]=3[N:19]3[CH:23]=[CH:22][CH:21]=[C:20]23)[CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 58551808HCID 58551808, compound

Product 1

HCID 58551585HCID 58551585, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3.15 g, 2.13 mL, 27.6 mmol) was added dropwise to a solution of methyl 3-hydroxy-4-pyrrol-1-yl-benzoate (3.00 g, 13.8 mmol) and tert-butyl 4-oxopiperidine-1-carboxylate (3.00 g, 15.2 mmol) in dichloromethane (60 mL) and the reaction mixture was stirred at room temperature for 6 hours. The reaction mixture was washed with water and 1N NaOH. The organics were dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography eluting with 0-30% EtOAc in Hexanes. The pure fractions were combined and concentrated to give 1′-tert-butyl 7-methyl spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′,7-dicarboxylate. ESI-MS m/z calc. 398.4. found 399.5 (M+1)+. Retention time: 2.13 minutes (3 min run).

Workup

  1. washThe reaction mixture was washed with water and 1N NaOH
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 0-30% EtOAc in Hexanes
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a409814fa418497f812c8feecfcc4790
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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