Dimethyl malonate → HCID 86597982, compound

HRID 2055830Notes

Reaction equation

HRID 2055830 reaction equation
[N+:1](/[CH:4]=[CH:5]/[C:6]1[CH:14]=[CH:13][C:9]2[O:10][CH2:11][O:12][C:8]=2[CH:7]=1)([O-:3])=[O:2].[C:15]([O:22][CH3:23])(=[O:21])[CH2:16][C:17]([O:19][CH3:20])=[O:18]>C1(C)C=CC=CC=1>[CH3:20][O:19][C:17]([CH:16]([CH:5]([C:6]1[CH:14]=[CH:13][C:9]2[O:10][CH2:11][O:12][C:8]=2[CH:7]=1)[CH2:4][N+:1]([O-:3])=[O:2])[C:15]([O:22][CH3:23])=[O:21])=[O:18]

Participants

4

Reactant 2

HCID 7943Dimethyl malonateHCID 6722963,4-Methylenedioxy-beta-nitrostyrene

Product 1

HCID 86597982HCID 86597982, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

[(S,S)-N-(pentamethylbenzenesulfonyl)-1,2-diphenyl-ethylenediamine](hexamethylbenzene)ruthenium (13.7 mg, 0.02 mmol, S/C=50), 5-[(1E)-2-nitroethenyl]-1,3-benzodioxole (193 mg, 1.0 mmol), dimethyl malonate (137 μl, 1.2 mmol) and toluene (4 ml) were added into Schlenk (20 ml) under an argon atmosphere, and stirred at 0° C. for 48 hours. The reaction solution was purified by flash column chromatography (hexane/acetone=90/10, SiO2), showing that the isolation yield of the product was 99%. The optical purity was measured by HPLC (CHIRALPACK AS-H manufactured by Daicel Co., Ltd., hexane:2-propanol=90:10, flow rate 1 m/min, detection by 210 nm), resulting to 95% ee.

Workup

  1. customThe reaction solution was purified by flash column chromatography (hexane/acetone=90/10, SiO2)
  2. customresulting to 95% ee

Sources & evidence

ORD record
ord-185a6c39be7343a1b78e60a4208e75b4
Source dataset
uspto-grants-2008_02
Patent number
US07332622B2

Reaction notes

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