Sodium Hydroxide → (+)-Dimethyl 5-oxo-3-(2,4,6-trimethoxyphenyl)pyrrolidine-2,4-dicarboxylate

HRID 553271Notes

Reaction equation

[N+:1]([CH:4]([C:27]([O:29][CH3:30])=[O:28])[CH:5]([C:15]1[C:20]([O:21][CH3:22])=[CH:19][C:18]([O:23][CH3:24])=[CH:17][C:16]=1[O:25][CH3:26])[CH:6]([C:11]([O:13][CH3:14])=[O:12])[C:7](OC)=[O:8])([O-])=O.[OH-].[Na+]>C(OCC)(=O)C>[O:8]=[C:7]1[NH:1][CH:4]([C:27]([O:29][CH3:30])=[O:28])[CH:5]([C:15]2[C:20]([O:21][CH3:22])=[CH:19][C:18]([O:23][CH3:24])=[CH:17][C:16]=2[O:25][CH3:26])[CH:6]1[C:11]([O:13][CH3:14])=[O:12]

Participants

Conditions

Temperature: 55 °C

Procedure

(+)-Trimethyl 3-nitro-2-(2,4,6-trimethoxyphenyl)propane-1,1,3-tricarboxylate (7.8 g, 0.018 mol) was dissolved in ethyl acetate (100 mL). To this solution, stannous chloride dihydrate (25 g, 0.118 mol) was added in portions over a period of 10 mins under stirring. The reaction mixture was heated to 55° C. for 2 hours. The mixture was cooled to 10° C., basified with 10% sodium hydroxide solution to pH 9, filtered through a celite pad and the pad washed with ethyl acetate (50 mL). The aqueous layer was extracted with ethyl acetate (2×100 mL). The organic layers were combined, dried over anhydrous sodium sulphate and concentrated under reduced pressure to give the title compound as a white solid.

Workup

temperatureThe mixture was cooled to 10° C.
filtrationfiltered through a celite pad
washthe pad washed with ethyl acetate (50 mL)
extractionThe aqueous layer was extracted with ethyl acetate (2×100 mL)
dry with materialdried over anhydrous sodium sulphate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-0aa81fbe3ac44666a012d53d74164028
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951961B2

Reaction notes

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