Benzylamine → HCID 46200115, compound

HRID 2065951Notes

Reaction equation

HRID 2065951 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.[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCOC(C)=O.CCCCCCC>C(Cl)Cl.[Pd]>[NH3:27].[CH2:20]([NH:27][CH:7]([CH3:16])/[CH:8]=[C:9](\[CH3:15])/[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

8

Reactant 4

HCID 7504BenzylamineHCID 8857Ethyl Acetate2×HCID 8900Heptane2×HCID 131730025HCID 131730025, compound

Product 2

HCID 222AmmoniaHCID 46200115HCID 46200115, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

Reaction of 17 (rac-Ethyl (2E)-4-(diethoxyphosphinyloxy)-2-methylpent-2-enoate) (188 mg, 0.60 mind) with BnNH2 (131 μL, 1.2 mmol) and 5 mol % [Pd] in CH2Cl2 (3.5 ml) at room temperature. MPLC (SiO2 with NH3 deactivated, AcOEt:heptane fraction 20:80) and preparative TLC (NH3-conditioned, AcOEt:heptane fraction 50:50) yield 18 (rac-Ethyl (2E)-N-benzyl-4-amino-2-methylpent-2-enoate) (98.7 mg, 67%) as a yellow oil.

Sources & evidence

ORD record
ord-252a29d81c51441d8c03e79c0530958e
Source dataset
uspto-grants-2012_10
Patent number
US08288566B2

Reaction notes

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