Tetrahydrofuran → 1-Benzyl-3-(phenylmethyl)-3-(2-hydroxyethyl)pyrrolidine

HRID 323269Notes

Reaction equation

HRID 323269 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([CH2:13][CH2:14][O:15][Si](C(C)(C)C)(C)C)[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C(OCC)(=O)C.O>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([CH2:13][CH2:14][OH:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 184648171-Benzyl-3-(phenylmethyl)-3-(2-(t-butyldimethylsilyloxy)ethyl)-2-oxopyrrolidineHCID 21226445Aluminium lithium hydride

Product 1

HCID 184645801-Benzyl-3-(phenylmethyl)-3-(2-hydroxyethyl)pyrrolidine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Combine 1-benzyl-3-(phenylmethyl)-3-(2-(t-butyldimethylsilyloxy)ethyl)-2-oxopyrrolidine (1.19 g, 2.81 mmol) and tetrahydrofuran (20 mL). Cool in an ice bath. Add dropwise a solution of lithium aluminum hydride (2.81 mL, 1 M in THF, 2.81 mmol). After the addition is complete, warm to ambient temperature. After 2 hours, heat to reflux. After 1 hour, cool to ambient temperature and cautiously add water (0.11 mL), a solution of 1 M sodium hydroxide (0.11 mL), and water (0.32 mL). Stir vigorously. After 2 hours, filter through celite and rinse with dichloromethane. Dry the filtrate over Na2SO4, filter, and concentrate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with ethyl acetate to give the title compound: Rf=0.34 (silica gel, 2% triethylamine/30% methanol/ethyl acetate).

Workup

  1. temperatureCool in an ice bath
  2. additionAfter the addition
  3. temperatureheat to reflux
  4. waitAfter 1 hour
  5. temperaturecool to ambient temperature
  6. waitAfter 2 hours
  7. filtrationfilter through celite
  8. washrinse with dichloromethane
  9. dry with materialDry the filtrate over Na2SO4
  10. filtrationfilter
  11. concentrationconcentrate in vacuo
  12. customto give a residue

Sources & evidence

ORD record
ord-ba23cb6371cb4a0e9a3916f1b39cf137
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

Loading…