Sodium Hydroxide → [1R*,8S*,9aR*]5,6-Dimethoxy-8-phenyl-2,3,7,8,9,9a-hexahydrophenalene-1-carboxylic acid

HRID 233409Notes

Reaction equation

HRID 233409 reaction equation
[C:1]([C@H:5]1[C@@H:16]2[C:17]3[C:8](=[CH:9][C:10]([O:26][CH3:27])=[C:11]([O:24][CH3:25])[C:12]=3[CH2:13][C@@H:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:15]2)[CH2:7][CH2:6]1)([O:3]C)=[O:2].[OH-].[Na+]>CO>[CH3:27][O:26][C:10]1[CH:9]=[C:8]2[C:17]3[C@H:16]([CH2:15][C@H:14]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:13][C:12]=3[C:11]=1[O:24][CH3:25])[C@H:5]([C:1]([OH:3])=[O:2])[CH2:6][CH2:7]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18641660[1R*,8S*,9aR*]1-Carbomethoxy-5,6-dimethoxy-8-phenyl-2,3,7,8,9,9a-hexahydrophenalene

Product 1

HCID 18641661[1R*,8S*,9aR*]5,6-Dimethoxy-8-phenyl-2,3,7,8,9,9a-hexahydrophenalene-1-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Crude [1R*,8S*,9aR*]1-Carbomethoxy-5,6-dimethoxy-8-phenyl-2,3,7,8,9,9a-hexahydrophenalene (0.8 g., 2.1 mmol), from Step 4, was dissolved in 100 mL of methanol and 8 mL of 1N aqueous sodium hydroxide solution was added. After stirring for 3 days at ambient temperature, the methanol was removed under reduced pressure. The residue was partitioned between 50 mL of diethyl ether and 75 mL of water. The aqueous phase was acidified to pH 2 with 6M aqueous hydrochloric acid solution and extracted with 3×25 mL of 1:1 ethyl acetate/diethyl ether. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give 0.74 g (100% yield) of the title compound as an oil; DCI MS: 253 (M+H)+. 1H NMR (CDCl3) δ:2.0-2.3 (m, 2H), 2.65-2.85 (m, 2H), 2.9-3.1 (m, 6H), 3.2-3.3 (m, 1H), 3.73 (s, 3H), 3.83 (s, 3H), 6.56 (s, 1H), 7.2-7.4 (m, 5H).

Workup

  1. customthe methanol was removed under reduced pressure
  2. customThe residue was partitioned between 50 mL of diethyl ether and 75 mL of water
  3. extractionextracted with 3×25 mL of 1:1 ethyl acetate/diethyl ether
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-616e1864650b47919ab10a3906c6ea0d
Source dataset
uspto-grants-1997_01
Patent number
US05591884

Reaction notes

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