Dibenzylamine → HCID 5368605, compound

HRID 2065948Notes

Reaction equation

HRID 2065948 reaction equation
[NH:1]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:16][CH2:17][O:18][C:19]([CH3:21])=[O:20].[CH3:22][CH2:23][CH2:24]CCCC>C(Cl)Cl.[Pd]>[CH2:9]([N:1]([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH:23]([CH3:24])/[CH:22]=[CH:21]/[C:19]([O:18][CH2:17][CH3:16])=[O:20])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 7656DibenzylamineHCID 21899848Ethylacetate heptane

Product 1

HCID 5368605HCID 5368605, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

Reaction of 30 (rac-Ethyl (2E)-4-(chloroacetoxy)pent-2-enoate) (221 mg, 1.0 mmol) with Bn2NH (383 μL, 2.0 mmol) and 8 mol % [Pd] in CH2Cl2 (10 ml) at room temperature according to Example 2. Flash chromatography (AcOEt heptane fraction 5:95) yields 12 (rac-Ethyl (2E)-N,N-dibenzyl-4-aminopent-2-enoate) (227 mg, 70%) as a colorless oil.

Sources & evidence

ORD record
ord-60fd55268e5141b3b6ff100415ecc3b9
Source dataset
uspto-grants-2012_10
Patent number
US08288566B2

Reaction notes

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