Diethyl Malonate → HCID 6999756, compound

HRID 1867946Notes

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]>>[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

Reactant 2

HCID 7761Diethyl Malonate

HCID 5284459beta-nitrostyrene, (E)-

Product 1

HCID 6999756HCID 6999756, compoundYield 83%

Procedure

To a mixture of trans-β-nitrostyrene (149 mg, 1.0 mmol) and diethyl malonate (0.304 ml, 2.0 mmol) was added, as an asymmetric catalyst, (R,R)-trans-1-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(N,N-dimethylamino)cyclohexyl]thiourea (20.7 mg, 0.05 mmol), obtained in Example 1A at room temperature under an argon atmosphere. After 12 hr, the reaction mixture was purified by preparative TLC (elution solvent: n-hexane/diethyl ether) to give the title compound as colorless needle crystals (257 mg, yield 83%, optical purity 88%).

Workup

customobtained in Example 1A at room temperature under an argon atmosphere
customthe reaction mixture was purified by preparative TLC (elution solvent: n-hexane/diethyl ether)

Sources & evidence

ORD record: ord-9e4a8b22aeba42e5a0b115f5cd1b2046
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07632970B2

Reaction notes

Loading…