Water → HCID 71008858, compound

HRID 1887490Notes

Reaction equation

HRID 1887490 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]2[C:13](=[O:28])[N:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[C:15](=[O:16])[CH:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O>CCO.ClCCl>[CH2:1]([N:8]1[CH2:9][CH:10]2[CH:15]([OH:16])[N:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:26])([F:27])[F:25])=[CH:19][CH:18]=3)[C:13](=[O:28])[CH:11]2[CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 71008634HCID 71008634, compound

Product 1

HCID 71008858HCID 71008858, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

To a cooled (−35˜−40° C.) solution of 5-Benzyl-2-(4-trifluoromethoxy-phenyl)-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione (0.6 g, 0.5 mmol) and CeCl3.7H2O (0.56 g, 0.5 mmol) in 250 mL EtOH/dichloromethane (1.5:1) were sequentially added NaBH4 (0.057 g, 10 mmol). The temperature was kept at −35˜−40° C. for 2 h, poured into cold water (100 mL) and extracted with dichloromethane (2×80 mL). After washing the organic phase with brine (100 mL) and drying over anhydrous Na2SO4, the solvent was removed and the crude product was purified by column chromatography on silica gel with petroleum ether/ethyl acetate (5:1 to 2:1) to yield the title compound (0.17 g, 29%). 1H NMR (300 MHz, CDCl3): δ 7.78 (d, 2H, J=9.0 Hz), 7.38-7.22 (m, 7H), 5.52 (d, 1H, J=6.9 Hz), 3.69 (q, 2H, J=12.6 Hz), 3.20-3.18 (m, 3H), 3.07 (bs, 1H), 2.52 (t, 1H, J=10.1 Hz), 2.31-2.28 (m, 1H); LC-MS: [M+1]+ 393.0.

Workup

  1. extractionextracted with dichloromethane (2×80 mL)
  2. washAfter washing the organic phase with brine (100 mL)
  3. dry with materialdrying over anhydrous Na2SO4
  4. customthe solvent was removed
  5. customthe crude product was purified by column chromatography on silica gel with petroleum ether/ethyl acetate (5:1 to 2:1)

Sources & evidence

ORD record
ord-d622314f496849e7813e86da0054df8a
Source dataset
uspto-grants-2013_08
Patent number
US08501768B2

Reaction notes

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