Water → 5-Methylene-2-(4-trifluoromethoxy-phenyl)-hexahydro-cyclopenta[c]pyrrol-1-one

HRID 1887496Notes

Reaction equation

HRID 1887496 reaction equation
O[CH:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=2)[C:5](=[O:18])[CH:4]2[CH2:19][C:20](=[CH2:22])[CH2:21][CH:3]12.[BH3-]C#N.[Na+].O>FC(F)(F)C(O)=O>[CH2:22]=[C:20]1[CH2:19][CH:4]2[C:5](=[O:18])[N:6]([C:7]3[CH:8]=[CH:9][C:10]([O:13][C:14]([F:16])([F:15])[F:17])=[CH:11][CH:12]=3)[CH2:2][CH:3]2[CH2:21]1

Participants

5

Reactant 3

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 866739173-Hydroxy-5-methylene-2-(4-trifluoromethoxy-phenyl)-hexahydro-cyclopenta[c]pyrrol-1-one

Product 1

HCID 866739185-Methylene-2-(4-trifluoromethoxy-phenyl)-hexahydro-cyclopenta[c]pyrrol-1-oneYield 42%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 3-Hydroxy-5-methylene-2-(4-trifluoromethoxy-phenyl)-hexahydro-cyclopenta[c]pyrrol-1-one (0.1 g, 0.32 mmol) in trifluoroacetic acid (20 mL) was added NaCNBH3 (0.04 g, 0.64 mmol) at −20° C., and the mixture was stirred for 1 h. Water (30 mL) was added. The mixture was extracted with dichloromethane (3×20 mL), washed with brine (50 mL), and dried over anhydrous Na2SO4. The solvent was removed by reduced pressure. The residue was purified by column chromatography on silica gel with petroleum ether/ethyl acetate (10:1 to 5:1) to yield the title compound (40 mg, 40%). 1H NMR (300 MHz, CDCl3): δ 7.69-7.64 (m, 2H), 7.25-7.19 (m, 2H), 4.91 (s, 2H), 4.07-4.01 (m, 1H), 3.54-3.49 (m, 1H), 3.19-3.12 (m, 1H), 2.96-2.71 (m, 4H), 2.25-2.18 (m, 1H); LC-MS: [M+1]+ 298.1.

Workup

  1. extractionThe mixture was extracted with dichloromethane (3×20 mL)
  2. washwashed with brine (50 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. customThe solvent was removed by reduced pressure
  5. customThe residue was purified by column chromatography on silica gel with petroleum ether/ethyl acetate (10:1 to 5:1)

Sources & evidence

ORD record
ord-394849c6648e4970b4d9061722407a28
Source dataset
uspto-grants-2013_08
Patent number
US08501768B2

Reaction notes

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