Dimethyl methylmalonate → Methyl 2-methoxycarbonyl-2-methyl-4-nitro-3-phenylbutanoate

HRID 2055832Notes

Reaction equation

HRID 2055832 reaction equation
[N+:1](/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([O-:3])=[O:2].[CH3:12][CH:13]([C:18]([O:20][CH3:21])=[O:19])[C:14]([O:16][CH3:17])=[O:15]>C1(C)C=CC=CC=1>[CH3:17][O:16][C:14]([C:13]([CH3:12])([CH:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:4][N+:1]([O-:3])=[O:2])[C:18]([O:20][CH3:21])=[O:19])=[O:15]

Participants

4

Reactant 2

HCID 69104Dimethyl methylmalonateHCID 5284459beta-nitrostyrene, (E)-

Product 1

HCID 23114487Methyl 2-methoxycarbonyl-2-methyl-4-nitro-3-phenylbutanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-20 °C

Procedure

[(S,S)-N-(pentamethylbenzenesulfonyl)-1,2-diphenyl-ethylenediamine](hexamethylbenzene)ruthenium (13.7 mg, 0.02 mmol, S/C=50), trans-β-nitrostyrene (149 mg, 1.0 mmol), dimethyl methylmalonate (160 μl, 1.2 mmol) and toluene (1 ml) were added into Schlenk (20 ml) under an argon atmosphere, and stirred at −20° 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 94%. The optical purity was measured by HPLC (CHIRALPACK AD manufactured by Daicel Co., Ltd., hexane:2-propanol=95:5, flow rate 0.5 m/min, detection by 210 nm), resulting to 97% ee.

Workup

  1. customThe reaction solution was purified by flash column chromatography (hexane/acetone=90/10, SiO2)
  2. customresulting to 97% ee

Sources & evidence

ORD record
ord-8f3321b1a2cc4dff98f5e632218d75ef
Source dataset
uspto-grants-2008_02
Patent number
US07332622B2

Reaction notes

Loading…