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

HRID 1887502Notes

Reaction equation

HRID 1887502 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH:13]3[CH2:15][C:16](=O)[CH2:17][CH:12]3[C:11]2=[O:19])=[CH:6][CH:5]=1.[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCl>[CH2:22]([NH:29][CH:16]1[CH2:17][CH:12]2[C:11](=[O:19])[N:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:21])[F:20])=[CH:5][CH:6]=3)[CH2:14][CH:13]2[CH2:15]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 710087992-(4-Trifluoromethoxy-phenyl)-hexahydro-cyclopenta[c]pyrrole-1,5-dione

Product 1

HCID 710087725-Benzylamino-2-(4-trifluoromethoxy-phenyl)-hexahydro-cyclopenta[c]pyrrol-1-oneYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-Trifluoromethoxy-phenyl)-hexahydro-cyclopenta[c]pyrrole-1,5-dione (0.5 g, 1.6 mmol) and benzylamine (0.34 g, 3.2 mmol) in dichloromethane (10 mL) were added NaBH(AcO)3 (1.0 g, 4.7 mmol). The mixture was stirred for 6 h at ambient temperature. The mixture was extracted with dichloromethane (2×15 mL), washed with brine (30 mL), dried over anhydrous Na2SO4. The solvent was removed, and the crude product was purified by silica column (MeOH/dichloromethane=1/30) to yield the title compound (0.4 g, 63%). 1H NMR (300 MHz, CDCl3): δ 7.67-7.63 (m, 2H), 7.32-7.07 (m, 7H), 4.08 (t, 1H, J=9.3 Hz), 3.76-3.56 (m, 3H), 3.34-3.31 (m, 1H), 3.16-3.09 (m, 1H), 2.88-2.83 (m, 1H), 2.21-2.02 (m, 3H), 1.65-1.58 (m, 1H).

Workup

  1. extractionThe mixture was extracted with dichloromethane (2×15 mL)
  2. washwashed with brine (30 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. customThe solvent was removed
  5. customthe crude product was purified by silica column (MeOH/dichloromethane=1/30)

Sources & evidence

ORD record
ord-42e26f4162b04c36835188c3966c415d
Source dataset
uspto-grants-2013_08
Patent number
US08501768B2

Reaction notes

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