Acetic Acid → (1R,2S)-Tranylcypromine

HRID 1619189Notes

Reaction equation

HRID 1619189 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[C:5](O)(=O)[CH3:6].[BH-](O[C:19]([CH3:21])=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+].[CH3:28][C:29]#N>>[CH2:3]1[C@@H:1]([NH2:4])[C@@H:2]1[C:6]1[CH:5]=[CH:21][CH:19]=[CH:29][CH:28]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 6342AcetonitrileHCID 69828CyclopropylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 19493(1R,2S)-Tranylcypromine

Conditions

Temperature
25 °C

Procedure

A solution of product obtained above (20 g, 89.7 mmol, 1.0 equiv.) in CH3CN (200 mL) was treated at 0° C. with cyclopropylamine (10.24 g, 179.4 mmol, 2.0 equiv), acetic acid (2 mL) and NaBH(OAc)3 (38 g, 179.4 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 (brine), dried (Na2SO4) and concentrated under reduced pressure to give the crude mixture of cis and trans amines. The mixture was separated by flash chromatography (SiO2) using 60% EtOAc/hexanes with 2.5% TEA to get rid of the undesired isomer (top spot). Further elution using 5% MeOH/DCM with 2.5% TEA gave 12.5 g of the trans amine as white solid.

Workup

  1. extractionextracted (10% MeOH/CH2Cl2)
  2. washThe organics were washed (brine)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customto give the crude
  6. customThe mixture was separated by flash chromatography (SiO2)
  7. customto get rid of the undesired isomer (top spot)
  8. washFurther elution

Sources & evidence

ORD record
ord-a7cfe94d2e944d188565ade684837e15
Source dataset
uspto-grants-2014_07
Patent number
US08772296B2

Reaction notes

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