HCID 59682332, compound → HCID 58641432, compound

HRID 1394952Notes

Reaction equation

[C:1]1([C@@H:7]2[CH:11]=[C:10](OS(C(F)(F)F)(=O)=O)[CH2:9][N:8]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:27]1([Mg]Br)[CH2:29][CH2:28]1>[Cu](I)I.C1COCC1>[CH:27]1([C:10]2[CH2:9][N:8]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@H:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:11]=2)[CH2:29][CH2:28]1

Participants

Conditions

Temperature: -10 °C

Procedure

Tert-butyl (2S)-2-phenyl-4-{[(trifluoromethyl)sulfonyl]oxy}-2,5-dihydro-1H-pyrrole-1-carboxylate (5-4, 100 mg, 0.254 mmol, 1 equiv) was added to a solution of dry THF (5 ml) containing copper iodide (5 mg, 0.025 mmol, 0.2 equiv) at −10° C. Cyclopropyl magnesium bromide (0.508 mL, 0.508 mmol, 2 equiv) was added drop wise and the resulting solution was stirred at −10° C. for 15 minutes. The reaction mixture was partitioned between aqueous ammonium chloride solution (15 mL) and ethyl acetate (3×10 mL). The combined organic layers were then dried over sodium sulfate, filtered, and concentrated to give tert-butyl (2S)-4-cyclopropyl-2-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate (32-1), which is converted to (2S)-4-cyclopropyl-N,N-dimethyl-2-phenyl-2,5-dihydro-1H-pyrrole-1-carboxamide (32-2) in the experimental mentioned above. 1H NMR (300 MHz, CDCl3) δ 7.22 (m, 5H), 5.82 (m, 1H), 5.35 (m, 1H), 4.43 (dd, J=14.5, 5.5 Hz, 1H), 4.00 (d, J=14.5 Hz, 1H), 2.82 (s, 6H), 1.40 (m, 1H), 0.76 (m, 2H), 0.54 (m, 2H). LRMS m/z (M+H) 257.2 found, 257.3 required.

Workup

customThe reaction mixture was partitioned between aqueous ammonium chloride solution (15 mL) and ethyl acetate (3×10 mL)
dry with materialThe combined organic layers were then dried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-240488a4e32d463183ad83a3b934b545
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348440B2

Reaction notes

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