1-Methyl-3-pyrrolidinol, (-)- → HCID 86602260, compound

HRID 458894Notes

Reaction equation

HRID 458894 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)([C:6]1[O:7][CH:8]=[CH:9][CH:10]=1)[OH:5].[CH3:18][N:19]1[CH2:23]C[C@@H:21](O)[CH2:20]1>C1(C)C=CC=CC=1>[CH3:18][N:19]1[CH2:20][CH2:21][C@@H:1]([O:2][C:3](=[O:17])[C:4]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)([C:6]2[O:7][CH:8]=[CH:9][CH:10]=2)[OH:5])[CH2:23]1

Participants

4

Reactant 2

HCID 69513321-Methyl-3-pyrrolidinol, (-)-HCID 669589942-Cyclohexyl-2-fur-2-yl-2-hydroxyacetic acid methyl ester

Product 1

HCID 86602260HCID 86602260, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5.0 g (0.021 mol) of 2-Cyclohexyl-2-fur-2-yl-2-hydroxyacetic acid methyl ester were dissolved in 150 ml of dry toluene. To this solution 2.12 g (0.021 mol) of (3R)-1-methylpyrrolidin-3-ol (Intermediate I-19) and 500 mg (0.021 mol) of HNa 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%→10%). Appropriate fractions were combined and evaporated to give 1.37 g (21%) of the title product 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%→10%)
  10. customevaporated

Sources & evidence

ORD record
ord-ef7dc212775743209fc7921f7945ddeb
Source dataset
uspto-grants-2007_03
Patent number
US07192978B2

Reaction notes

Loading…