trans-Methyl 2-(dibenzylamino)cycloheptanecarboxylate → trans-Methyl 2-aminocycloheptanecarboxylate acetate

HRID 1011537Notes

Reaction equation

HRID 1011537 reaction equation
C([N:8](CC1C=CC=CC=1)[C@@H:9]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[C:16]([O:18][CH3:19])=[O:17])C1C=CC=CC=1>C(O)(=O)C.[Pd]>[C:16]([OH:18])(=[O:17])[CH3:10].[NH2:8][C@@H:9]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[C:16]([O:18][CH3:19])=[O:17]

Participants

4

Reactant 1

HCID 59497788trans-Methyl 2-(dibenzylamino)cycloheptanecarboxylate

Product 1

HCID 66669572trans-Methyl 2-aminocycloheptanecarboxylate acetateYield 147.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

trans-Methyl 2-(dibenzylamino)cycloheptanecarboxylate (1.04 g, 2.94 mmol) was hydrogenated at 50 psi in 20 mL glacial acetic acid with 500 mg 10% palladium on carbon for 25 h. The reaction was filtered through celite and concentrated to yield trans-methyl 2-aminocycloheptanecarboxylate acetate (500 mg, 99%). 1H NMR (400 MHz, CDCl3) δ ppm 3.71 (3H, s), 3.35-3.44 (1H, m), 2.59 (1H, td, J=8.62, 3.15 Hz), 1.84-1.96 (2H, m), 1.61-1.80 (4H, m), 1.41-1.60 (4H, m). MS [M+H]+=171.94.

Workup

  1. filtrationThe reaction was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-db2f08f920a74055952e5e24c8e822e4
Source dataset
uspto-grants-2011_07
Patent number
US07977362B2

Reaction notes

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