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 2299197Notes

Reaction equation

HRID 2299197 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, 1H), 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-126810e337494d9abb94a85e8507f85b
Source dataset
uspto-grants-2002_12
Patent number
US06495560B1

Reaction notes

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