Sodium Carbonate → (R)-2-hydroxymethyl-1-(4-pyrrolidinophenethyl)pyrrolidine

HRID 2251887

Reaction equation

HRID 2251887 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][C@@H:2]1[CH2:3][OH:4].S(O[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:17][CH:16]=1)(=O)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[OH:4][CH2:3][C@H:2]1[CH2:5][CH2:6][CH2:7][N:1]1[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2724541Prolinol, (R)-HCID 229341624-Pyrrolidinophenethyl mesylate

Product 1

HCID 69198126(R)-2-hydroxymethyl-1-(4-pyrrolidinophenethyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

D-Prolinol (2.72 g, 25.0 mmol), 4-pyrrolidinophenethyl mesylate (6.06 g, 22.5 mmol) and sodium carbonate (3.45 g, 25.0 mmol) were added to acetonitrile (150 ml), and they were heated at 90° C. under reflux for 3.5 hours. The reaction mixture was cooled to room temperature and then filtered. The filtrate was concentrated to dryness under reduced pressure, and the residue was distributed into ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. 1 M hydrochloric acid was added to the organic layer and pH of the aqueous layer was kept at 1 to extract the intended product in the aqueous layer. 4 M sodium hydroxide was added to the aqueous layer to adjust pH of the aqueous layer to 14, and the intended product was extracted from the precipitates thus formed with ethyl acetate. The extract was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain (R)-2-hydroxymethyl-1-(4-pyrrolidinophenethyl)pyrrolidine in the form of a light yellow oily substance (4.96 g, 85%).

Workup

  1. temperatureunder reflux for 3.5 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated to dryness under reduced pressure
  5. addition1 M hydrochloric acid was added to the organic layer and pH of the aqueous layer
  6. extractionto extract the intended product in the aqueous layer
  7. addition4 M sodium hydroxide was added to the aqueous layer
  8. extractionthe intended product was extracted from the
  9. customprecipitates thus
  10. customformed with ethyl acetate
  11. dry with materialThe extract was dried over magnesium sulfate
  12. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1481601ebcc54261acad07139cfe134a
Source dataset
uspto-grants-2008_01
Patent number
US07320973B2

Linked notes

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