Pyrrolidine → tert-Butyl 6-bromo-4-oxospiro[chroman-2,4'-piperidine]-1'-carboxylate

HRID 420149Notes

Reaction equation

HRID 420149 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].N1CCCC1.[CH3:20][C:21]([C:23]1[CH:28]=[C:27]([Br:29])[CH:26]=[CH:25][C:24]=1O)=[O:22]>CO>[Br:29][C:27]1[CH:28]=[C:23]2[C:24](=[CH:25][CH:26]=1)[O:14][C:11]1([CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][CH2:10]1)[CH2:20][C:21]2=[O:22]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 959915'-Bromo-2'-hydroxyacetophenoneHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 2794759tert-Butyl 6-bromo-4-oxospiro[chroman-2,4'-piperidine]-1'-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

60 mL of MeOH, 7.97 g of N-Boc-piperidin-4-one, and 3.34 mL of pyrrolidine were added to 8.60 g of 5-bromo-2-hydroxyacetophenone put in a 200-mL flask equipped with a condenser, and the mixture was overnight heated under reflux. The reaction mixture was cooled to room temperature, and concentrated. The residue was purified through silica gel column chromatography (eluted with n-hexane/EtOAc=6/1) to obtain the intended compound as a pale yellow solid.

Workup

  1. customput in a 200-mL flask
  2. customequipped with a condenser
  3. temperatureheated
  4. temperatureunder reflux
  5. concentrationconcentrated
  6. customThe residue was purified through silica gel column chromatography (eluted with n-hexane/EtOAc=6/1)

Sources & evidence

ORD record
ord-44fd7053516d4802b45f8f5001d14f31
Source dataset
uspto-grants-2012_01
Patent number
US08093389B2

Reaction notes

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