Cyclopropylamine → (1R,2S)-Tranylcypromine

HRID 1619191Notes

Reaction equation

HRID 1619191 reaction equation
O=[C:2]1[CH2:7][CH2:6][C:5]([CH2:14][CH2:15][C:16]#[N:17])(C2C=NC=CN=2)[CH2:4][CH2:3]1.C1(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>[CH2:15]1[C@@H:16]([NH2:17])[C@@H:14]1[C:5]1[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 69828CyclopropylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 59030601HCID 59030601, compound

Product 1

HCID 19493(1R,2S)-TranylcypromineYield 33%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3-(4-oxo-1-(pyrazin-2-yl)cyclohexyl)propanenitrile (610 mg, 2.7 mmol, 1.0 equiv) in acetonitrile (10 mL) was treated with cyclopropylamine (380 μL, 5.3 mmol, 2.0 equiv), acetic acid (0.1 mL) and NaBH(OAc)3 (1.1 g, 5.3 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. Purification of the crude material by flash chromatography (SiO2, 70-80% EtOAc/hexanes containing 2.5% triethylamine) gave 0.24 g of the trans amine (0.89 mmol, 33%) and then further elution afforded 0.24 g of the cis amine (0.89 mmol, 33%).

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. customPurification of the crude material by flash chromatography (SiO2, 70-80% EtOAc/hexanes containing 2.5% triethylamine)

Sources & evidence

ORD record
ord-32cc7214feb2431d815a41a047e798c6
Source dataset
uspto-grants-2014_07
Patent number
US08772296B2

Reaction notes

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