Potassium Carbonate → (S)-1-(3-hydroxypropyl)pyrrolidine-2-carboxamide

HRID 2227959Notes

Reaction equation

HRID 2227959 reaction equation
Br[CH2:2][CH2:3][CH2:4][OH:5].[NH:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[C:11]([NH2:13])=[O:12].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:5][CH2:4][CH2:3][CH2:2][N:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[C:11]([NH2:13])=[O:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 111306L-Prolinamide

Product 1

HCID 45116058(S)-1-(3-hydroxypropyl)pyrrolidine-2-carboxamideYield 60.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Bromo-1-propanol (584 mg, 4.2mmol) was added to a mixture of (S)-pyrrolidine-2-carboxamide (399 mg, 3.5 mmol) and potassium carbonate (966 mg, 7 mmol) in acetonitrile (10 ml). The mixture was heated at reflux for 5 hours and the mixture was stirred for 18 hours at ambient temperature. The insolubles were removed by filtration and the solvent was removed from the filtrate by evaporation The residue was purified by column chromatography on silica eluting with methylene chloride/methanol (9/1 followed by 8/2) to give (S)-1-(3-hydroxypropyl)-pyrrolidine-2-carboxamide (365 mg, 60%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 5 hours
  3. customThe insolubles were removed by filtration
  4. customthe solvent was removed from the filtrate by evaporation The residue
  5. customwas purified by column chromatography on silica eluting with methylene chloride/methanol (9/1 followed by 8/2)

Sources & evidence

ORD record
ord-d223f06ea214413888fd21d05c28b555
Source dataset
uspto-grants-2002_07
Patent number
US06414148B1

Reaction notes

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