Cyclopropylamine → (1R,2S)-Tranylcypromine

HRID 1619187Notes

Reaction equation

HRID 1619187 reaction equation
OC[C:3]1([C:10]2[CH:15]=[CH:14]C=CN=2)[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.C1([NH2:19])CC1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.C(O)(=O)C>[CH2:14]1[C@@H:15]([NH2:19])[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 59030629HCID 59030629, compound

Product 1

HCID 19493(1R,2S)-Tranylcypromine

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 4-(hydroxymethyl)-4-(pyridin-2-yl)cyclohexanone (410 mg, 2.0 mmol, 1.0 equiv) in 1,2-dichloroethane (15 mL) was treated at 0° C. with cyclopropylamine (280 uL, 4.0 mmol, 2 equiv), acetic acid (0.1 mL) and NaBH(OAc)3 (848 mg, 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. The crude material was purified by flash column chromatography (SiO2, 5% MeOH/CH2Cl2 containing 2.5% NH4OH) to provide the trans amine. Further elution afforded the cis amine.

Workup

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

Sources & evidence

ORD record
ord-823ca1f65dd243ada74cccd9dfc53320
Source dataset
uspto-grants-2014_07
Patent number
US08772296B2

Reaction notes

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