Reaction #1833265

ord-f948984bd4f44557996c440bc0891544

Reaction equation

N[C@@H]1C[C@H]1c1ccccc1
(trans)-2-phenylcyclopropanamine
N[C@@H]1C[C@H]1c1ccccc1
intermediate A
N[C@@H]1C[C@H]1c1ccccc1
(trans)-2-phenylcyclopropanamine
O=C([O-])[O-].[K+].[K+]
K2CO3
→
CC(C)(C)OC(=O)N[C@@H]1C[C@H]1c1ccccc1
tert-butyl(trans)-2-phenylcyclopropylcarbamate
Yield 189.3%

Reactants

N[C@@H]1C[C@H]1c1ccccc1
(trans)-2-phenylcyclopropanamine
N[C@@H]1C[C@H]1c1ccccc1
intermediate A
N[C@@H]1C[C@H]1c1ccccc1
(trans)-2-phenylcyclopropanamine
O=C([O-])[O-].[K+].[K+]
K2CO3

Reagents

None

Solvents

C1CCOC1
THF

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherAfter removal of the solvent, CH2Cl2
  2. 2
    workup.ADDITIONwas added
  3. 3
    Washwashed with a saturated solution of NaHCO3 and brine
  4. 4
    ExtractionThe organic layer was extracted
  5. 5
    Dryingdried with MgSO4
  6. 6
    Filtrationfiltered
  7. 7
    OtherThe crude was purified by silica gel chromatography (Hexane-MTBE 90:10)

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%

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09149447B2uspto-grants-2015_10