Hydrochloric Acid → N-Methyl-N-{[(2S)-pyrrolidin-2-yl]methyl}cyclopropanamine

HRID 1359836Notes

Reaction equation

HRID 1359836 reaction equation
[CH:1]1([N:4]([CH3:12])[C:5]([C@@H:7]2[CH2:11][CH2:10][CH2:9][NH:8]2)=O)[CH2:3][CH2:2]1.B.Cl>C1COCC1>[CH:1]1([N:4]([CH3:12])[CH2:5][C@@H:7]2[CH2:11][CH2:10][CH2:9][NH:8]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 45115984HCID 45115984, compound

Product 1

HCID 45088411N-Methyl-N-{[(2S)-pyrrolidin-2-yl]methyl}cyclopropanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-pyrrolidine-2-carboxylic acid cyclopropyl-methyl-amide in THF at 0° C. was added borane (2 eq., 1 M in THF) dropwise. The mixture was allowed to warm up to rt then heated to reflux for 24 hours. The cooled reaction was acidified with HCl and heated at 75° C. for 10 mins. The mixture was concentrated, basified with 2N NaOH and extracted with 10% methanol in DCM. The combined DCM was dried and concentrated to give cyclopropyl-methyl-(S)-1-pyrrolidin-2-ylmethyl-amine.

Workup

  1. temperaturethen heated
  2. temperatureto reflux for 24 hours
  3. customThe cooled reaction
  4. temperatureheated at 75° C. for 10 mins
  5. concentrationThe mixture was concentrated
  6. extractionextracted with 10% methanol in DCM
  7. dry with materialThe combined DCM was dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1998fe8a4a4649789a08a85818c97b1a
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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