Hydrochloric Acid → HCID 69627816, compound

HRID 1359699Notes

Reaction equation

HRID 1359699 reaction equation
[CH:1]1([NH:4][C:5]([C@H:7]2[CH2:11][CH2:10][CH2:9][NH:8]2)=O)[CH2:3][CH2:2]1.Cl>C1COCC1>[CH:1]1([NH:4][CH2:5][C@H:7]2[CH2:11][CH2:10][CH2:9][NH:8]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21139077(R)-N-Cyclopropylpyrrolidine-2-carboxamide

Product 1

HCID 69627816HCID 69627816, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)-Pyrrolidine-2-carboxylic acid cyclopropylamide (0.5 g, 3.2 mmol) in THF (4 mL) was added to borane-tetrahydrofuran complex (6 mL, 1 M, 6 mmol) at 0° C. The reaction mixture was refluxed for overnight after which more BH3 was added and heating was continued for another 2 h. The reaction mixture was acidified with 3M HCl soution and refluxed for 0.5 h. The reaction mixture was concentrated and the residue was basified with 2M NaOH solution. It crude reaction mixture was then extracted with 5% methanol in dichloromethane to give 0.4 g (89%) of cyclopropyl-(R)-1-pyrrolidin-2-ylmethyl-amine.

Workup

  1. temperatureThe reaction mixture was refluxed for overnight after which more
  2. additionwas added
  3. temperatureheating
  4. temperaturerefluxed for 0.5 h
  5. concentrationThe reaction mixture was concentrated
  6. customIt crude reaction mixture
  7. extractionwas then extracted with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-b1898f5138054662b97a8edf331b9543
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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