Pyrrolidine → 6-Bromo-3'-isopropylspiro[chroman-2,1'-cyclopentan]-4-one

HRID 2096552Notes

Reaction equation

HRID 2096552 reaction equation
[CH:1]([CH:4]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5]1)([CH3:3])[CH3:2].[Br:10][C:11]1[CH:12]=[CH:13][C:14](O)=[C:15]([C:17](=[O:19])[CH3:18])[CH:16]=1.N1CCCC1>CO>[Br:10][C:11]1[CH:16]=[C:15]2[C:14](=[CH:13][CH:12]=1)[O:9][C:6]1([CH2:7][CH2:8][CH:4]([CH:1]([CH3:3])[CH3:2])[CH2:5]1)[CH2:18][C:17]2=[O:19]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 959915'-Bromo-2'-hydroxyacetophenoneHCID 125705723-(Propan-2-yl)cyclopentan-1-one

Product 1

HCID 584237926-Bromo-3'-isopropylspiro[chroman-2,1'-cyclopentan]-4-oneYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-isopropylcyclopentanone (0.5 g, 3.962 mmol), 1-(5-bromo-2-hydroxyphenyl)ethanone (0.424 g, 1.98 mmol) and pyrrolidine (0.143 g, 1.98 mmol) in MeOH (25 mL) was refluxed overnight. The solvent was removed in vacuo to give crude 6-bromo-3′-isopropylspiro[chroman-2,1′-cyclopentan]-4-one (500 mg, 79%). 1H-NMR (CDCl3): 0.78 (m, 3H), 0.82 (m, 3H), 1.34 (m, 1H), 1.58 (m, 3H), 1.75 (m, 1H), 1.91 (m, 2H), 2.08 (m, 1H0, 2.73 (s, 2H), 6.74 (m, 1H), 7.44 (m, 1H), 7.89 (d, 1H).

Workup

  1. temperaturewas refluxed overnight
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e8b99d9a2aee4cd38b1671c3d2d952fd
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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