HCID 68490281, compound → HCID 68494343, compound

HRID 1944225Notes

Reaction equation

HRID 1944225 reaction equation
C(O)(=O)C.[CH2:5]([O:7][C:8]1[CH:17]=[C:16]2[CH:11]([CH2:12][CH2:13][N:14]([CH2:18][C:19]3[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=3)[CH2:15]2)[CH2:10][C:9]=1[O:31]CC1C=CC=CC=1)[CH3:6]>C(O)C>[CH2:5]([O:7][C:8]1[CH:17]=[C:16]2[CH:11]([CH2:12][CH2:13][N:14]([CH2:18][C:19]3[CH:20]=[C:21]([O:29][CH3:30])[C:22]([O:27][CH3:28])=[C:23]([O:25][CH3:26])[CH:24]=3)[CH2:15]2)[CH2:10][C:9]=1[OH:31])[CH3:6]

Participants

3

Reactant 1

HCID 68490281HCID 68490281, compound

Product 1

HCID 68494343HCID 68494343, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7-Ethoxy-6-benzyloxy-2-(3,4,5-trimethoxybenzyl)-tetrahydroisoquinoline acetate (307 mg, 0.66 mmol) was dissolved in ethanol and ethyl acetate (5 mL each), degassed, treated with 10% Pd/C (50 mg) then placed under an atmosphere of hydrogen. After 0.5 h no starting material was evident by TLC and the reaction was filtered through celite and evaporated. The resultant oil was precipitated from ethyl acetate/hexane to give a yellow powder (240 mg, 97%). 1H NMR δ 1.39 (3H, t, J 7.0), 2.68 (2H, t, J 5.7), 2.75 (2H, t, J 5.7), 3.52 (2H, s), 3.58 (2H, s), 3.83 (3H, s), 3.84 (6H, s), 4.01 (2H, q, J 7.0), 5.50 (1H, br), 6.46 (1H, s), 6.61 (2H, s) and 6.67 (1H, s).

Workup

  1. customethyl acetate (5 mL each), degassed
  2. additiontreated with 10% Pd/C (50 mg)
  3. filtrationthe reaction was filtered through celite
  4. customevaporated
  5. customThe resultant oil was precipitated from ethyl acetate/hexane

Sources & evidence

ORD record
ord-a720d4b447e545dfa10fcbca90007140
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

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