Potassium Hydroxide → HCID 22287005, compound

HRID 1987233Notes

Reaction equation

HRID 1987233 reaction equation
[OH-].[K+].FC(F)(F)C([N:7]1[CH2:15][C@@H:14]2[C@H:9]([CH2:10][C:11]3[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=3[CH2:13]2)[CH2:8]1)=O>CO>[CH2:8]1[CH:9]2[CH:14]([CH2:13][C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[CH2:10]2)[CH2:15][NH:7]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86602690HCID 86602690, compound

Product 1

HCID 22287005HCID 22287005, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of potassium hydroxide (8.67 g, 154.6 mmol) in 100 mL of methanol was trans-2-trifluoroacetyl-2,3,3a,4,9,9a-hexahydro-1H-benz[f]isoindole (8.32 g, 30.91 mmol), and the mixture was stirred at room temperature for four hours. The mixture was concentrated in-vacuo, and the residue was partitioned between diethyl ether and water. The layers were separated, and the aqueous phase was extracted with three 200 mL portions of diethyl ether. The combined organic phases were dried over sodium sulfate, and concentrated in-vacuo to a yellow oil. The oil was purified by flash chromatography on an 8×15 cm silica column, eluting with a 40:10:1 mixture of methylene chloride, methanol, and 25% aqueous ammonium hydroxide. Obtained 2.5 g of the trans isomer as a white solid, and 2.0 g of the cis isomer as a pale yellow solid. Yield=46% (trans), 37% (cis). NMR (trans) (300 MHz, CDCl3) δ 7.12 (m, 4H), 3.36-3.31 (m, 2H), 3.08-3.03 (m, 2H), 2.71-2.58 (m, 4H), 2.46 (bs, 1H), 1.90 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated in-vacuo
  2. customthe residue was partitioned between diethyl ether and water
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with three 200 mL portions of diethyl ether
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. concentrationconcentrated in-vacuo to a yellow oil
  7. customThe oil was purified by flash chromatography on an 8×15 cm silica column
  8. washeluting with a 40:10:1 mixture of methylene chloride, methanol, and 25% aqueous ammonium hydroxide
  9. customObtained 2.5 g of the trans isomer as a white solid, and 2.0 g of the cis isomer as a pale yellow solid

Sources & evidence

ORD record
ord-1d91eb8978134c38a3ecd73684e8dbb8
Source dataset
uspto-grants-2009_06
Patent number
US07550500B2

Reaction notes

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