HCID 54674497, compound → HCID 54674650, compound

HRID 2402749Notes

Reaction equation

HRID 2402749 reaction equation
[CH3:1][Mg]I.[F:4][C:5]([F:22])([F:21])[C:6]1[N:11]=[C:10]([N:12]2[CH2:16][C@@H:15]3[C:17](=[O:20])[CH2:18][CH2:19][C@@H:14]3[CH2:13]2)[CH:9]=[CH:8][CH:7]=1>CCOCC>[CH3:1][C@:17]1([OH:20])[C@@H:15]2[C@@H:14]([CH2:13][N:12]([C:10]3[CH:9]=[CH:8][CH:7]=[C:6]([C:5]([F:4])([F:21])[F:22])[N:11]=3)[CH2:16]2)[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 54674497HCID 54674497, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 54674650HCID 54674650, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Methylmagnesium iodide in ether (0.302 mL, 0.907 mmol) was added to (3aR,6aS)-2-[6-(trifluoromethyl)pyridin-2-yl]hexahydrocyclopenta[c]pyrrol-4(1H)-one (70 mg, 0.259 mmol) from Example 32 in ether (0.1 mL) at 25° C., and the reaction mixture was stirred for 1 hour. The reaction was quenched with saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The combined organic washes were purified by silica gel chromatography using 0-30% ethyl acetate/hexane as eluent to give the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 7.46 (t, J=7.9, 1H), 6.93 (d, J=7.2, 1H), 6.50 (d, J=8.6, 1H), 5.92 (s, 1H), 4.03 (dd, J=11.1, 3.7, 1H), 3.69 (t, J=9.4, 1H), 3.61-3.50 (m, 1H), 3.43 (dd, J=10.0, 5.7, 1H), 2.83-2.69 (m, 1H), 2.46 (td, J=9.0, 3.9, 1H), 2.14-2.02 (m, 1H), 1.90 (dq, J=11.6, 8.4, 1H), 1.79-1.62 (m, 2H), 1.42 (s, 3H); MS (ESI+) m/z 287 (M+H)+.

Workup

  1. customThe reaction was quenched with saturated aqueous ammonium chloride solution
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe combined organic washes were purified by silica gel chromatography

Sources & evidence

ORD record
ord-d043033675a445d1a061cb1f41d5df7d
Source dataset
uspto-grants-2014_08
Patent number
US08796470B2

Reaction notes

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