Potassium Carbonate → HCID 15381986, compound

HRID 1746083Notes

Reaction equation

HRID 1746083 reaction equation
[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]([O-:14])([O-])=[O:12].[K+].[K+]>C1COCC1>[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[NH:10][C:11](=[O:12])[O:14][C:1]([CH3:7])([CH3:6])[CH3:2])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 19493(1R,2S)-Tranylcypromine2×

Product 1

HCID 15381986HCID 15381986, compoundYield 189.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Over a solution of (trans)-2-phenylcyclopropanamine (intermediate A, 1.14 g, 1 eq) in 50 mL of THF, 1.25 g (1.05 eq) of K2CO3 was added and stirred 3 hours at room temperature. After removal of the solvent, CH2Cl2 was added, then washed with a saturated solution of NaHCO3 and brine. The organic layer was extracted, dried with MgSO4 and filtered. The crude was purified by silica gel chromatography (Hexane-MTBE 90:10) affording 1.89 g of tert-butyl(trans)-2-phenylcyclopropylcarbamate. Yield: 95%

Workup

  1. customAfter removal of the solvent, CH2Cl2
  2. additionwas added
  3. washwashed with a saturated solution of NaHCO3 and brine
  4. extractionThe organic layer was extracted
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customThe crude was purified by silica gel chromatography (Hexane-MTBE 90:10)

Sources & evidence

ORD record
ord-f948984bd4f44557996c440bc0891544
Source dataset
uspto-grants-2015_10
Patent number
US09149447B2

Reaction notes

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