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

HRID 38473

Reaction equation

HRID 38473 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[OH:11])=[O:3].[C:12]([N:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].N1CCCC1.CO>O>[Br:10][C:8]1[CH:9]=[C:4]2[C:5](=[CH:6][CH:7]=1)[O:11][C:22]1([CH2:23][CH2:24][N:19]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:20][CH2:21]1)[CH2:1][C:2]2=[O:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 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 962WaterSolvent

Procedure

A mixture of 5-bromo-2-hydroxyacetophenone (104 g, 485 mmol), N-Boc-piperidin-4-one (98.6 g, 494 mmol), 20 mL of pyrrolidine (17.3 g, 243 mmol) and 261 mL of MeOH was heated under reflux until the reaction was complete. The mixture was cooled, then 87 mL of H2O were added, and the mixture was filtered and dried to give intended compound as a colorless solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux until the reaction
  3. temperatureThe mixture was cooled
  4. filtrationthe mixture was filtered
  5. customdried
  6. customto give

Sources & evidence

ORD record
ord-de58866a73cb48c7a016ae38f2f5ffeb
Source dataset
uspto-grants-2013_09
Patent number
US08524730B2

Linked notes

Loading…