Potassium Carbonate → HCID 54674620, compound

HRID 2363612Notes

Reaction equation

HRID 2363612 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[CH2:6][N:7]1[CH2:11][C@@H:10]2[C@@H:12]([NH2:15])[CH2:13][CH2:14][C@@H:9]2[CH2:8]1.Br[CH:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:22]([NH:15][C@@H:12]1[C@@H:10]2[C@@H:9]([CH2:8][N:7]([CH2:6][C:5]3[CH:16]=[CH:17][CH:18]=[C:3]([C:2]([F:19])([F:1])[F:20])[CH:4]=3)[CH2:11]2)[CH2:14][CH2:13]1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 236603BromodiphenylmethaneHCID 66591105HCID 66591105, compound

Product 1

HCID 54674620HCID 54674620, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(3aR,4S,6aS)-2-(3-(Trifluoromethyl)benzyl)octahydrocyclopenta[c]pyrrol-4-amine (60 mg, 0.211 mmol), from Example 156 Step A was combined with (bromomethylene)dibenzene (62.6 mg, 0.253 mmol) and potassium carbonate (87 mg, 0.633 mmol) in N,N-dimethylformamide (1 mL). The reaction was stirred at room temperature for 72 hours. The reaction was quenched with water and extracted with diethyl ether. The ether extracts were washed with water (3×1 mL) and the solvent removed. The crude material was purified using a 12 g silica gel cartridge eluting with a gradient of 0-3% methanol (2 N ammonia)/dichloromethane to give (3aR,4S,6aS)-N-benzhydryl-2-(3-(trifluoromethyl)benzyl)octahydrocyclopenta[c]pyrrol-4-amine: 1H NMR (500 MHz, pyridine-d5) δ ppm 7.71 (s, 1H), 7.64-7.59 (m, 4H), 7.52 (d, J=7.7, 1H), 7.44 (t, J=7.7, 1H), 7.33 (td, J=7.6, 4.7, 4H), 7.25-7.21 (m, 4H), 5.09 (s, 1H), 3.51 (q, J=13.5, 2H), 3.02 (dd, J=12.9, 5.5, 1H), 2.63-2.54 (m, 1H), 2.51 (dd, J=8.8, 2.8, 1H), 2.47-2.41 (m, 1H), 2.37 (t, J=8.0, 1H), 2.32-2.25 (m, 2H), 1.98 (td, J=11.4, 5.6, 1H), 1.89 (ddd, J=12.7, 10.4, 5.8, 1H), 1.45 (ddd, J=14.7, 11.9, 8.1, 1H), 1.32-1.23 (m, 1H); MS (ESI+) m/z 451 (M+H)+.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with diethyl ether
  3. washThe ether extracts were washed with water (3×1 mL)
  4. customthe solvent removed
  5. customThe crude material was purified
  6. washeluting with a gradient of 0-3% methanol (2 N ammonia)/dichloromethane

Sources & evidence

ORD record
ord-c5d1ccbd69c140829cfb9bc5da299626
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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