Hydrochloric Acid → (R)-(-)-1-(2-Pyrrolidinylmethyl)pyrrolidine

HRID 478929

Reaction equation

HRID 478929 reaction equation
N1CCC[C@H]1[C:3]([C@H:5]1[CH2:9][CH2:8][CH2:7][NH:6]1)=O.Cl.[OH-].[Na+]>C1COCC1>[N:6]1([CH2:3][C@H:5]2[CH2:9][CH2:8][CH2:7][NH:6]2)[CH2:7][CH2:8][CH2:9][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 693271912-(R)-Prolylpyrrolidine

Product 1

HCID 853151(R)-(-)-1-(2-Pyrrolidinylmethyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

2-(R)-Prolylpyrrolidine (1.2 g, 7.1 mmol) was dissolved in THF (10 ml). The reaction mixture was cooled to 0° C. and BH3, 1M in THF (10 ml, 10 mmol) was dropwise at 0 C. The reaction mixture was refluxed for 16 h, 3 M HCl (4.7 ml). 2 M NaOH solution was added until pH 10 was reached. The product was extracted with 5% MeOH in CH2Cl2 (three times). The organic layers were dried over Na2SO4 and the solvent was removed to provide the title compound as a slightly yellow liquid (73%), which was used without further purification for the next step.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. extractionThe product was extracted with 5% MeOH in CH2Cl2 (three times)
  3. dry with materialThe organic layers were dried over Na2SO4
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-ff3d358a37914d5692b06abcb1443767
Source dataset
uspto-grants-2003_11
Patent number
US06642232B2

Linked notes

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