Diethyl Malonate → HCID 6999756, compound

HRID 1867945Notes

Reaction equation

HRID 1867945 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]urea (7.9 mg, 0.02 mmol) obtained in Example 1B 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/ethyl acetate=5/1) to give the title compound as colorless needle crystals (53.8 mg, 87%, 91% ee). The yield and optical purity are shown in Table 1.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by preparative TLC (elution solvent: n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-22855919125c44ffada856e8af6893fd
Source dataset
uspto-grants-2009_12
Patent number
US07632970B2

Reaction notes

Loading…