Potassium Carbonate → (S)-3-hydroxy-1-(4-pyrrolidinophenethyl)pyrrolidine

HRID 2251902Notes

Reaction equation

S(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1)(=O)(=O)C.Cl.[NH:20]1[CH2:24][CH2:23][C@H:22]([OH:25])[CH2:21]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:25][C@H:22]1[CH2:23][CH2:24][N:20]([CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:10][CH:9]=2)[CH2:21]1

Participants

Conditions

Temperature: 90 °C

Procedure

4-Pyrrolidinophenethyl mesylate (13.45 g, 50.0 mmol), (S)-3-pyrrolidinol hydrochloride (5.56 g, 45.0 mmol) and potassium carbonate (18.63 g, 135 mmol) were added to acetonitrile (200 ml), and they were heated at 90° C. for 3 hours. The reaction mixture was cooled and then filtered. The filtrate was evaporated to dryness 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 aqueous layer was neutralized and then the product was again extracted with ethyl acetate. The organic layer was dried and the solvent was evaporated under reduced pressure to obtain (S)-3-hydroxy-1-(4-pyrrolidinophenethyl)pyrrolidine in the form of a light yellow solid (6.30 g, 52%).

Workup

temperatureThe reaction mixture was cooled
filtrationfiltered
customThe filtrate was evaporated to dryness under reduced pressure
extractionThe intended product was extracted from the ethyl acetate layer with 1 M hydrochloric acid
extractionthe product was again extracted with ethyl acetate
customThe organic layer was dried
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-138df2b0b96a49639ae1365f6f7adff0
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07320973B2

Reaction notes

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