HCID 22591816, compound → Methyl 1-(3-aminophenyl)-5-oxopyrrolidine-3-carboxylate

HRID 22901Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:14](=[O:15])[CH2:13][CH:12]([C:16]([O:18][CH3:19])=[O:17])[CH2:11]2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>C(OCC)(=O)C.[Pt]=O>[NH2:1][C:4]1[CH:5]=[C:6]([N:10]2[C:14](=[O:15])[CH2:13][CH:12]([C:16]([O:18][CH3:19])=[O:17])[CH2:11]2)[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 23 °C

Procedure

Platinum oxide (202.6 mg, 0.89 mmol, 0.05 equiv) was added to a solution of methyl 1-(3-nitrophenyl)-5-oxopyrrolidine-3-carboxylate (4.2014 g, 15.9 mmol, 1 equiv) in ethyl acetate (170 mL). The resulting suspension was placed under a hydrogen balloon and was stirred at 23° C. for 18 hr. The reaction was filtered through celite and was concentrated in vacuo to give the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.15 (t, 1H, J=2.1 Hz), 7.13 (t, 1H, J=8.1 Hz), 6.78 (dd, 1H, J=8.1 Hz, 1.5 Hz), 6.49 (dd, 1H, J=8.0 Hz, 1.7 Hz), 4.07 (dd, 1H, J=10.0 Hz, 6.8 Hz), 3.99 (dd, 1H, J=10.0 Hz, 8.7 Hz), 3.77 (s, 3H), 3.75 (br s, 2H), 3.29-3.38 (m, 1H), 2.92 (dd, 1H, J=17.3 Hz, 7.8 Hz), 2.84 (dd, 1H, J=17.3 Hz, 9.7 Hz). MS: (+) 235.0 (M+H), 469.5, 703.5; (−) 293.5, 527.0.

Workup

filtrationThe reaction was filtered through celite
concentrationwas concentrated in vacuo

Sources & evidence

ORD record: ord-a9eb895e93bd4eee92924d3c0257a103
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06849639B2

Reaction notes

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