Reaction #1833269

ord-f3047937a8fc4b37a3c12bafcc61cb5b

Reaction equation

N[C@@H]1C[C@H]1c1ccc(OCc2ccccc2)cc1
Intermediate D
N[C@@H]1C[C@H]1c1ccc(OCc2ccccc2)cc1
(Trans)-2-[4-(benzyloxy)phenyl]cyclopropanamine
O=[N+]([O-])[C@@H]1C[C@H]1c1ccc(Br)cc1
1-bromo-4-[(trans)-2-nitrocyclopropyl]benzene
O=[N+]([O-])[C@@H]1C[C@H]1c1ccc(Br)cc1
intermediate F
O=[N+]([O-])[C@@H]1C[C@H]1c1ccc(Br)cc1
1-bromo-4-[(trans)-2-nitrocyclopropyl]benzene
→
N[C@@H]1C[C@H]1c1ccc(Br)cc1
(trans)-2-(4-bromophenyl)cyclopropanamine
Yield 10.0%

Reactants

N[C@@H]1C[C@H]1c1ccc(OCc2ccccc2)cc1
Intermediate D
N[C@@H]1C[C@H]1c1ccc(OCc2ccccc2)cc1
(Trans)-2-[4-(benzyloxy)phenyl]cyclopropanamine
O=[N+]([O-])[C@@H]1C[C@H]1c1ccc(Br)cc1
1-bromo-4-[(trans)-2-nitrocyclopropyl]benzene
O=[N+]([O-])[C@@H]1C[C@H]1c1ccc(Br)cc1
intermediate F
O=[N+]([O-])[C@@H]1C[C@H]1c1ccc(Br)cc1
1-bromo-4-[(trans)-2-nitrocyclopropyl]benzene

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThis compound was synthesized

Procedure

This compound was synthesized using the same methodology described in Intermediate D, using as starting material 1-bromo-4-[(trans)-2-nitrocyclopropyl]benzene (intermediate F). Yield: 10%. 1HNMR (CD3OD): 1.45 (m, 2H), 2.61 (m, 1H), 2.86 (m, 1H), 6.98 (d, 2H), 7.11 (d, 2H). MS (M+H): 211.9.

Source

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