Dimethyl malonate → Propanedioic acid, [1-(4-methylphenyl)-2-nitroethyl]-, dimethyl ester

HRID 2055827Notes

Reaction equation

[CH3:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[C:13]([O:20][CH3:21])(=[O:19])[CH2:14][C:15]([O:17][CH3:18])=[O:16]>C1(C)C=CC=CC=1>[CH3:18][O:17][C:15]([CH:14]([CH:6]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:12][CH:11]=1)[CH2:7][N+:8]([O-:10])=[O:9])[C:13]([O:20][CH3:21])=[O:19])=[O:16]

Participants

Conditions

Temperature: 30 °C

Procedure

[(S,S)-N-(4-tert-butylbenzenesulfonyl)-1,2-diphenylethylenediamine](hexamethylbenzene)ruthenium (12.9 mg, 0.02 mmol, S/C=50), 4-methyl-β-nitrostyrene (184 mg, 1.0 mmol), dimethyl malonate (114 μl, 1.0 mmol) and toluene (1 ml) were added into Schlenk (20 ml) under an argon atmosphere, and stirred at 30° C. for 24 hours. 1HNMR determination of the solution showed that the yield of the product was 51%. The reaction solution was purified by flash column chromatography (hexane/acetone=80/20, SiO2), and the optical purity was measured by HPLC (CHIRALPACK AD manufactured by Daicel Co., Ltd., hexane:2-propanol=90:10, flow rate 0.5 ml/min, detection by 210 nm), resulting to 82% ee.

Workup

customThe reaction solution was purified by flash column chromatography (hexane/acetone=80/20, SiO2)
customresulting to 82% ee

Sources & evidence

ORD record: ord-0145cdf5c1a842c3afaa520b2aaf79cd
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07332622B2

Reaction notes

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