Acetic Acid → (1R,2S)-Tranylcypromine

HRID 1619186Notes

Reaction equation

HRID 1619186 reaction equation
OC[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7]C(=O)CC1.C1([NH2:19])CC1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.CCOC(C)=O>[CH2:7]1[C@@H:8]([NH2:19])[C@@H:3]1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 69828CyclopropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 215146764-(Hydroxymethyl)-4-phenylcyclohexan-1-one

Product 1

HCID 19493(1R,2S)-Tranylcypromine

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 4-(hydroxymethyl)-4-phenylcyclohexanone (5.0 g, 24.5 mmol, 1.0 equiv.) in 1,2-dichloroethane (50 mL) was treated at 0° C. with cyclopropylamine (4.2 g, 74.0 mmol, 3.0 equiv.), 1 mL acetic acid and NaBH(OAc)3 (15.6 g, 74.0 mmol, 3.0 equiv.) successively. After being stirred at 25° C. for 12 h, the reaction mixture was diluted (EtOAc), washed (1×1 N aqueous NaOH and 2× brine), dried (Na2SO4) and concentrated under reduced pressure. Purification by flash chromatography (SiO2, 50% EtOAc/n-Hexane with 5% TEA) gave the trans amine isomer (the bottom spot on the TLC).

Workup

  1. washwashed (1×1 N aqueous NaOH and 2× brine)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customPurification by flash chromatography (SiO2, 50% EtOAc/n-Hexane with 5% TEA)

Sources & evidence

ORD record
ord-88520ebde5b743edaa90b567baf39fd5
Source dataset
uspto-grants-2014_07
Patent number
US08772296B2

Reaction notes

Loading…