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

HRID 1359742Notes

Reaction equation

HRID 1359742 reaction equation
[N:1]1([C:6]([C@H:8]2[CH2:12][CH2:11][CH2:10][NH:9]2)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>C1COCC1>[N:1]1([CH2:6][C@H:8]2[CH2:12][CH2:11][CH2:10][NH:9]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10034997(R)-Pyrrolidin-2-YL-pyrrolidin-1-YL-methanone

Product 1

HCID 853151(R)-(-)-1-(2-Pyrrolidinylmethyl)pyrrolidineYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of pyrrolidin-1-yl-(R)-pyrrolidin-2-yl-methanone (1.2 g, 7.1 mmol) in THF (10 mL) at 0° C. was added BH3 (10 mL, 10 mmol). The mixture was heated to reflux for 16 hours. The reaction was acidified with HCl and concentrated. The residue was basified to pH 10 with 2N NaOH and extracted with 5% methanol in DCM. The organic layer was concentrated and purified on a silica gel column to give 800 mg (73%) of (R)-2-pyrrolidin-1-ylmethyl-pyrrolidine.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 16 hours
  3. concentrationconcentrated
  4. extractionextracted with 5% methanol in DCM
  5. concentrationThe organic layer was concentrated
  6. custompurified on a silica gel column

Sources & evidence

ORD record
ord-83b40e70203c47ae8018ef209b198db5
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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