Cyclopropylamine → (1R,2S)-Tranylcypromine

HRID 1619190Notes

Reaction equation

HRID 1619190 reaction equation
OC[C:3]1([C:10]2[CH:15]=[N:14]C=CN=2)[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.[CH:16]1(N)CC1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(#N)C.C(O)(=O)C>[CH2:16]1[C@@H:15]([NH2:14])[C@@H:10]1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 69828CyclopropylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 59030591HCID 59030591, compound

Product 1

HCID 19493(1R,2S)-TranylcypromineYield 42%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 4-(hydroxymethyl)-4-(pyrazin-2-yl)cyclohexanone (360 mg, 2.0 mmol, 1.0 equiv) in acetonitrile (4 mL) was treated with cyclopropylamine (280 μL, 4.0 mmol, 2.0 equiv), acetic acid (0.1 mL) and NaBH(OAc)3 (848 mg, 4.0 mmol, 2.0 equiv) successively. After being stirred at 25° C. for 12 h, the reaction mixture was carefully diluted (sat.NaHCO3) and extracted (10% MeOH/CH2Cl2). The organics were washed with brine, dried with Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash column chromatography (SiO2, EtOAc containing 2.5% NH4OH then EtOAc/5% MeOH containing 2.5% NH4OH, the second spot was collected) to provide 180 mg of trans amine as a white solid (0.70 mmol, 42%).

Workup

  1. extractionextracted (10% MeOH/CH2Cl2)
  2. washThe organics were washed with brine
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by flash column chromatography (SiO2, EtOAc containing 2.5% NH4OH
  6. customEtOAc/5% MeOH containing 2.5% NH4OH, the second spot was collected)

Sources & evidence

ORD record
ord-cd3e4159d6184bd0a91286d904f4e43c
Source dataset
uspto-grants-2014_07
Patent number
US08772296B2

Reaction notes

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