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

HRID 518146Notes

Reaction equation

HRID 518146 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>[C:15]([O:14][C:12]([N:19]1[CH2:24][CH2:23][C:22]2([CH2:1][C:2](=[O:3])[C:4]3[C:5](=[CH:6][CH:7]=[C:8]([Br:10])[CH:9]=3)[O:11]2)[CH2:21][CH2:20]1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

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'-carboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-hydroxy-5-bromoacetophenone (10.75 g, 50 mmol), N—BOC-4-piperidone (9.96 g, 50 mmol) and pyrrolidine (2.09 ml, 25 mmol) in MeOH (80 ml) was heated to reflux for 11 h. The solvent was removed under vacuum and the crude mixture was purified by column chromatography (eluent: hexane/AcOEt 90:10 to 80:20) to give 6-bromo-4-oxo-spiro[chromane-2,4′-piperidine]-1′-carboxylic acid tert-butyl ester (18.55 g) as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 11 h
  3. customThe solvent was removed under vacuum
  4. customthe crude mixture was purified by column chromatography (eluent: hexane/AcOEt 90:10 to 80:20)

Sources & evidence

ORD record
ord-53e9ed24be7f4a63b4e09f54f05a9a4e
Source dataset
uspto-grants-2015_08
Patent number
US09115148B2

Reaction notes

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