P-Anisidine → HCID 131730026, compound

HRID 2065952Notes

Reaction equation

HRID 2065952 reaction equation
C(OP(OCC)(O[CH:7]([CH3:16])/[CH:8]=[C:9](\[CH3:15])/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=O)C.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=1.CCCCCCC>C(Cl)Cl.[Pd]>[C:10]([O:12][CH:13]([CH3:14])[CH3:20])([CH3:9])=[O:11].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28]/[C:8](/[CH2:7][CH3:16])=[C:9](\[CH3:15])/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:24][CH:23]=1

Participants

7

Reactant 3

HCID 7732P-AnisidineHCID 8900HeptaneHCID 131730025HCID 131730025, compound

Product 2

HCID 7915Isopropyl AcetateHCID 131730026HCID 131730026, compoundYield 182.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

Reaction of 17 (rac-Ethyl (2E)-4-(diethoxyphosphinyloxy)-2-methylpent-2-enoate) (188 mg, 0.60 mmol) with p-anisidine (148 mg, 1.2 mmol) and 5 mol % [Pd] in CH2Cl2 (3.5 ml) at room temperature. Flash chromatography (AcOiPr:heptane fraction 15:85 to 20:80) yields 19 (rac-Ethyl (2E)-N-(4-methoxyphenyl)-4-amino-2-methylpent-2-enoate) (144 mg, 91) as a yellow oil.

Sources & evidence

ORD record
ord-408f47280de54cbb8d4cec4d6cf3413b
Source dataset
uspto-grants-2012_10
Patent number
US08288566B2

Reaction notes

Loading…