Dichloromethane → (S)-ethyl 3-methyl-2-(2H-pyrrol-1(5H)-yl)butanoate

HRID 2069485

Reaction equation

HRID 2069485 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[C@H:5]([CH:7]([CH3:9])[CH3:8])[NH2:6])[CH3:2].ClCCl.Cl[CH2:15]/[CH:16]=[CH:17]\[CH2:18]Cl.CCCCCC>CCCCCC.C(OCC)(=O)C>[CH3:8][CH:7]([CH3:9])[C@H:5]([N:6]1[CH2:18][CH:17]=[CH:16][CH2:15]1)[C:4]([O:3][CH2:1][CH3:2])=[O:10]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8058HexaneHCID 87182l-Valine, ethyl esterHCID 64321151,4-Dichloro-cis-2-butene

Product 1

HCID 59180252(S)-ethyl 3-methyl-2-(2H-pyrrol-1(5H)-yl)butanoateYield 52%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

From L-valine ethyl ester (1.0 g, 6.9 mmol), dichloromethane (1 ml) and cis-1,4-dichloro-2-butene (250 mg, 2.0 mmol). Flash chromatography: silica gel, gradient neat hexane to hexane:ethyl acetate (1:2) afforded the product (205 mg, 52%) as yellow oil.

Sources & evidence

ORD record
ord-4462479e4b25449b885dae1bf5bcd500
Source dataset
uspto-grants-2012_10
Patent number
US08299113B2

Linked notes

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