Diethyl Malonate → HCID 6999756, compound

HRID 1867944Notes

Reaction equation

HRID 1867944 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].[C:12]([O:20][CH2:21][CH3:22])(=[O:19])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]>C1(C)C=CC=CC=1>[CH2:21]([O:20][C:12]([CH:13]([C@@H:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:4][N+:1]([O-:3])=[O:2])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:19])[CH3:22]

Participants

4

Reactant 2

HCID 7761Diethyl MalonateHCID 5284459beta-nitrostyrene, (E)-

Product 1

HCID 6999756HCID 6999756, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution (0.40 ml) of trans-β-nitrostyrene (29.8 mg, 0.20 mmol) and diethyl malonate (0.061 ml, 0.40 mmol) in toluene was added, as an asymmetric catalyst, (R,R)-trans-1-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(N,N-dimethylamino)cyclohexyl]thiourea (8.2 mg, 0.02 mmol) obtained in Example 1A at room temperature under an argon atmosphere. After 24 hr, the reaction mixture was concentrated under reduced pressure. The residue was purified by preparative TLC (elution solvent: n-hexane/diethyl ether) to give the title compound as colorless needle crystals (53.3 mg, yield 86%). The yield and optical purity are shown in Tables 1-3. melting point: 45-47° C. (n-hexane/diethyl ether)

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by preparative TLC (elution solvent: n-hexane/diethyl ether)

Sources & evidence

ORD record
ord-ff32e8499c5e4d56bef994b54d8eed04
Source dataset
uspto-grants-2009_12
Patent number
US07632970B2

Reaction notes

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