Methyl 9-hydroxy-9H-fluorene-9-carboxylate → HCID 86602259, compound

HRID 458893

Reaction equation

HRID 458893 reaction equation
[CH3:1][O:2][C:3]([C:5]1([OH:18])[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:4].[CH3:19][N:20]1[CH2:24]C[C@@H:22](O)[CH2:21]1>C1(C)C=CC=CC=1>[CH3:19][N:20]1[CH2:21][CH2:22][C@@H:1]([O:2][C:3]([C:5]2([OH:18])[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:11]3[C:6]2=[CH:7][CH:8]=[CH:9][CH:10]=3)=[O:4])[CH2:24]1

Participants

4

Reactant 2

HCID 267210Methyl 9-hydroxy-9H-fluorene-9-carboxylateHCID 69513321-Methyl-3-pyrrolidinol, (-)-

Product 1

HCID 86602259HCID 86602259, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.980 g (0.0041 mol) of 9-Hydroxy-9H-fluorene-9-carboxylic acid methyl ester were dissolved in 30 ml of toluene. To this solution 0.412 g (0.0041 mol) of (3R)-1-methylpyrrolidin-3-ol (Intermediate I-19) and a catalitic amount of Na(0) were added and the mixture was refluxed using a Dean-Stark system for 24 hours. The reaction mixture was cooled, and extracted with HCl 2N. The aqueous layer was basified with K2CO3 and extracted with AcOEt (3×100 ml). The organic layers were combined, dried over Na2SO4 and evaporated to dryness to yield a residue which was purified by chromatography on silica gel eluting with chloroform plus isopropanol (0%→20%). Appropiate fractions were combined and evaporated to give 0.390 g (31%) of the title compound as an oil.

Workup

  1. temperaturethe mixture was refluxed
  2. customfor 24 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with HCl 2N
  5. extractionextracted with AcOEt (3×100 ml)
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness
  8. customto yield a residue which
  9. customwas purified by chromatography on silica gel eluting with chloroform plus isopropanol (0%→20%)
  10. customevaporated

Sources & evidence

ORD record
ord-9aafd057259845989f66878dd37d866a
Source dataset
uspto-grants-2007_03
Patent number
US07192978B2

Linked notes

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