Methyl 5-oxo-L-prolinate → HCID 86760067, compound

HRID 1823206Notes

Reaction equation

[NH:1]1[C@H:5]([C:6]([O:8][CH3:9])=[O:7])[CH2:4][CH2:3][C:2]1=[O:10].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:21]([O:25][C:26](=[O:33])[C:27]([C:30](Cl)=[O:31])=[N+:28]=[N-:29])([CH3:24])([CH3:23])[CH3:22]>C1COCC1>[CH3:9][O:8][C:6]([C@@H:5]1[CH2:4][CH2:3][C:2](=[O:10])[N:1]1[C:30](=[O:31])[C:27]([C:26]([O:25][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:33])=[N+:28]=[N-:29])=[O:7]

Participants

Conditions

Temperature: -78 °C

Procedure

In a flask methyl(s)-(+)-2 pyrrolidone-5-carboxylate (1.0 g, 6.99 mmol) was dissolved in 40 mL THF and cooled to −78° C. LHMDS (8.0 mL, 8.0 mmol) 1.0M in THF was added and the reaction stirred at −78° C. for 25 mins. The chlorocarbonyl-diazo-acetic acid tert-butyl ester (1.7 g, 8.39 mmol, J. Org. Chem. 1994, 59, 1418) was then slowly added and the reaction stirred at −78° C. for 1.5 h, quenched at −78° C. with 5% citric acid and let warm to room temperature. Diluted with EtOAc, seperated, extracted 2× with EtOAc, washed with brine, and dried with magnesium sulfate. Concentrated under vacuum and purified by flash chromatography (10–30% EtOAc/hexanes) to give the product as a viscous yellow oil (1.1 g, 65%). 1HNMR (300 MHz, CDCl3) δ 1.51 (s, 9H) 2.1(m, 1H) 2.2–2.8 (m, 3H) 3.79 (s, 3H) 4.74 (dd, 1H, J 4.0 8.8).

Workup

stirringthe reaction stirred at −78° C. for 1.5 h
customquenched at −78° C. with 5% citric acid
temperaturelet warm to room temperature
additionDiluted with EtOAc
customseperated
extractionextracted 2× with EtOAc
washwashed with brine
dry with materialdried with magnesium sulfate
concentrationConcentrated under vacuum
custompurified by flash chromatography (10–30% EtOAc/hexanes)

Sources & evidence

ORD record: ord-e1c9fce6845548b8b8c315e01d5cc231
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07037911B2

Reaction notes

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