ethyl (+/-)-10,11-dihydro-3-methoxy-11-oxo-5H-dibenzo[a,d]cycloheptene-10-acetate → Ethyl (+/-)-10,11 dihydro-3-methoxy-5H-dibenzo[a,d]cycloheptene-10-acetate

HRID 1369226Notes

Reaction equation

HRID 1369226 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:12](=O)[CH:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]3[CH:20]=[CH:21][CH:22]=[CH:23][C:9]=3[CH2:8][C:7]=2[CH:24]=1>C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]3[CH:20]=[CH:21][CH:22]=[CH:23][C:9]=3[CH2:8][C:7]=2[CH:24]=1

Participants

4

Reactant 1

HCID 18340680ethyl (+/-)-10,11-dihydro-3-methoxy-11-oxo-5H-dibenzo[a,d]cycloheptene-10-acetate

Product 1

HCID 15462070Ethyl (+/-)-10,11 dihydro-3-methoxy-5H-dibenzo[a,d]cycloheptene-10-acetateYield 86.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl (±)-10,11-dihydro-3-methoxy-11-oxo-5H-dibenzo[a,d]cycloheptene-10-acetate (0.3 g., 0.93 mmol) and 10% Pd/C (0.3 g) in glacial acetic acid (25 mL) was hydrogenated at 50 psi for 18 hours. The mixture was filtered using celite® and washed with acetic acid. The filtrate was concentrated and reconcentrated from toluene and methylene chloride to give 0.25 g of the title compound: 1H NMR (400 MHz, CDCl3) δ1.28 (t, 3H), 2.60 (m, 2H), 2.90 (m, 1H), 3.30 (m, 1H), 3.80 (s, 3H), 3.85 (d, 1H), 4.18 (q, 2H), 4.30 (d, 1H), 6.70 (m, 2H), 7.0 (d, 1 H), 7.22 (m, 4H).

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with acetic acid
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-883ba2cbb1e94f87a24428b36bf2224e
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

Loading…