Sodium cyanoborohydride → HCID 71009029, compound

HRID 1887491Notes

Reaction equation

HRID 1887491 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]2[CH:13]([OH: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)[CH:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH3-]C#N.[Na+]>FC(F)(F)C(O)=O>[CH2:1]([N:8]1[CH2:9][CH:10]2[CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:25])[F:26])=[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

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 71008858HCID 71008858, compound

Product 1

HCID 71009029HCID 71009029, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 5-Benzyl-3-hydroxy-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[3,4-c]pyrrol-1-one (6.0 g, 15.3 mmol) in trifluoroacetic acid (50 mL) was added NaCNBH3 (1.0 g, 15.3 mmol) and the mixture was stirred at room temperature overnight. Trifluoroacetic acid was removed by reduced pressure and the residue was added to dichloromethane (50 mL). Saturate solution of Na2CO3 (70 mL) was added. The mixture was extracted with dichloromethane (2×60 mL), washed with brine (100 mL), dried over Na2SO4. The solvent was removed and the crude product was purified by column chromatography on silica gel with petroleum ether:ethyl acetate (10:1 to 5:1) to yield the title compound (4.0 g, 70%). 1H NMR (300 MHz, CDCl3): δ 7.73-7.69 (m, 2H), 7.31-7.22 (m, 7H), 4.04 (t, 1H, J=9.5 Hz), 3.74-3.54 (m, 3H), 3.28-3.17 (m, 2H), 2.95 (bs, 1H), 2.76-2.74 (m, 1H), 2.63-2.53 (m, 2H); LC-MS: [M+1]+ 376.9.

Workup

  1. customTrifluoroacetic acid was removed by reduced pressure
  2. additionthe residue was added to dichloromethane (50 mL)
  3. additionSaturate solution of Na2CO3 (70 mL) was added
  4. extractionThe mixture was extracted with dichloromethane (2×60 mL)
  5. washwashed with brine (100 mL)
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed
  8. customthe crude product was purified by column chromatography on silica gel with petroleum ether:ethyl acetate (10:1 to 5:1)

Sources & evidence

ORD record
ord-e8615bfffedf4d0fbfed7f1d3b679e94
Source dataset
uspto-grants-2013_08
Patent number
US08501768B2

Reaction notes

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