Sodium Iodide → (R)-1-(4-dimethylaminophenethyl)-3-hydroxypyrrolidine

HRID 1859449Notes

Reaction equation

S(C1C=CC(C)=CC=1)(O[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH3:15])[CH3:14])=[CH:9][CH:8]=1)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].[OH:31][C@@H:32]1[CH2:36][CH2:35][NH:34][CH2:33]1>C(#N)C>[CH3:15][N:13]([CH3:14])[C:10]1[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][N:34]2[CH2:35][CH2:36][C@@H:32]([OH:31])[CH2:33]2)=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 90 °C

Procedure

4-Dimethylaminophenethyl tosylate (1.91 g, 6.0 mmol), sodium carbonate (750 mg, 7.0 mmol) and sodium iodide (40 mg, 0.26 mmol) were added to a solution of (R)-3-hydroxypyrrolidine (522 mg, 6.0 mmol) in acetonitrile (40 ml), and they were heated under reflux at 90° C. for 4 hours. The solvent was evaporated under reduced pressure. The obtained residue was distributed in 2 M NaOH and chloroform. The organic layer was dried and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography. The product was eluted with dichloromethane, then with dichloromethane and methanol (50:1) and finally with a mixture of the same solvents (20:1). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to obtain (R)-1-(4-dimethylaminophenethyl)-3-hydroxypyrrolidine in the form of a light yellow oil (1.00 g, 71%).

Workup

temperaturewere heated
customThe solvent was evaporated under reduced pressure
customThe organic layer was dried
customthe solvent was evaporated under reduced pressure
washThe product was eluted with dichloromethane
additionwith dichloromethane and methanol (50:1) and finally with a mixture of the same solvents (20:1)
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-d32f0010ef0e40e5a2bfeb0acd9db396
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528504B2

Reaction notes

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