Cyclopropylamine → [(R)-1-(5-Bromo-pyridin-2-yl)-pyrrolidin-3-yl]-cyclopropyl-amine

HRID 423403Notes

Reaction equation

HRID 423403 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][CH2:11][C@H:10](OS(C)(=O)=O)[CH2:9]2)=[N:6][CH:7]=1.[CH:18]1([NH2:21])[CH2:20][CH2:19]1>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][CH2:11][C@@H:10]([NH:21][CH:18]3[CH2:20][CH2:19]3)[CH2:9]2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 69828CyclopropylamineHCID 86638154methanesulfonic acid (S)-1-(5-bromo-pyridin-2-yl)-pyrrolidin-3-yl ester

Product 1

HCID 66673109[(R)-1-(5-Bromo-pyridin-2-yl)-pyrrolidin-3-yl]-cyclopropyl-amineYield 61.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve methanesulfonic acid (S)-1-(5-bromo-pyridin-2-yl)-pyrrolidin-3-yl ester (3.07 g, 9.48 mmol) and cyclopropylamine (1.7 mL, 23.68 mmol) in THF (20 mL). Microwave the mixture at 130° C. for 6 h. Dilute the mixture with EtOAc (100 mL) and wash with saturated NaHCO3 (25 mL). Dry the organic portion over Na2SO4, filter, and concentrate. Purify the crude material by chromatography, eluting with a gradient of 75-100% EtOAc/hexane to give 1.638 g (61%) of the title compound. LC-MS/ES m/z (79Br) 283.0 [M+H]+.

Workup

  1. washwash with saturated NaHCO3 (25 mL)
  2. dry with materialDry the organic portion over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the crude material by chromatography
  6. washeluting with a gradient of 75-100% EtOAc/hexane

Sources & evidence

ORD record
ord-745b8b3e18d846b79c855d0f8f90b2f4
Source dataset
uspto-grants-2012_01
Patent number
US08101764B2

Reaction notes

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