Pyrrolidine → HCID 58423879, compound

HRID 2096560Notes

Reaction equation

HRID 2096560 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[C:12]([CH:16]1[CH2:20][CH2:19][C:18](=O)[CH2:17]1)([CH3:15])([CH3:14])[CH3:13].N1CCCC1>CO>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:11][C:18]1([CH2:19][CH2:20][CH:16]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:17]1)[CH2:9][C:8]2=[O:10]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 959915'-Bromo-2'-hydroxyacetophenoneHCID 3167693-(TERT-BUTYL)CYCLOPENTANONE

Product 1

HCID 58423879HCID 58423879, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(5-bromo-2-hydroxy-phenyl)-ethanone (573 mg, 2.68 mmol), 3-tert-butylcyclopentanone (750 g, 5.36 mol) and pyrrolidine (362 mg, 5.092 mol) in methanol was refluxed overnight. The reaction mixture was removed in vacuo. The residue was diluted with an equal volume of H2O and then added HCl until pH=1. The mixture was extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered, and evaporated to give 6-bromo-3′-tert-butylspiro[chroman-2,1′-cyclopentan]-4-one (0.8 g, 89%). 1H NMR (CDCl3): 0.77 (s, 9H), 1.34 (m, 1H), 1.48 (m, 2H), 1.63 (m, 2H), 1.81 (m, 2H), 2.09 (m, 2H), 2.72 (m, 2H), 6.73 (t, 1H), 7.47 (d, 1H), 7.89 (s, 1H).

Workup

  1. temperaturewas refluxed overnight
  2. customThe reaction mixture was removed in vacuo
  3. additionThe residue was diluted with an equal volume of H2O
  4. extractionThe mixture was extracted with EtOAc
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-aa0f852e474a486d89230859012529ca
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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