Potassium Carbonate → (S)-3-hydroxy-1-(3-pyrrolidinophenethyl)pyrrolidine
Reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([CH:32]=[CH:33][CH:34]=2)[CH2:9][CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][C@@H:12]2CN2C3C=CC=CC=3COC3C=CC=CC2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.N1CC[C@H]([OH:41])C1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:41][C@H:13]1[CH2:14][CH2:15][N:11]([CH2:10][CH2:9][C:8]2[CH:32]=[CH:33][CH:34]=[C:6]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:7]=2)[CH2:12]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
3-Pyrrolidinophenethyl mesylate (1.80 g, 4.00 mmol) synthesized in Example 21, (S)-3-pyrrolidinol hydrochloride (0.50 g, 4.05 mmol) and potassium carbonate (1.70 g, 12.3 mmol) were added to acetonitrile (20 ml), and they were heated at 100° C. for 12 hours. Acetonitrile was evaporated under reduced pressure, and the residue was distributed into water and ethyl acetate. The intended product was extracted from the ethyl acetate layer with 1 M hydrochloric acid. The extract was neutralized and then the product was extracted with ethyl acetate. The organic layer was dried and the solvent was evaporated under reduced pressure to obtain (S)-3-hydroxy-1-(3-pyrrolidinophenethyl)pyrrolidine in the form of a light yellow solid (1.04 g, 100%).
Workup
- customAcetonitrile was evaporated under reduced pressure
- extractionThe intended product was extracted from the ethyl acetate layer with 1 M hydrochloric acid
- extractionthe product was extracted with ethyl acetate
- customThe organic layer was dried
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-7e676270ee5947caa3b5646c02022d38
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07320973B2
Reaction notes
Loading…