N-Methylbenzylamine → HCID 18948459, compound

HRID 1768601Notes

Reaction equation

HRID 1768601 reaction equation
[O:1]1[CH2:23][CH:2]1[CH2:3][CH:4]([CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[CH3:24][NH:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CO>[CH2:26]([N:25]([CH2:23][CH:2]([OH:1])[CH2:3][CH:4]([CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:9])[CH3:10])=[O:6])[CH3:24])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 7669N-MethylbenzylamineHCID 18948434HCID 18948434, compound

Product 1

HCID 18948459HCID 18948459, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.39 g (7.65 mmole) of t-butyl 4,5-epoxy-2-(1-naphthylmethyl)pentanoate (prepared as described in Preparation 11) were reacted with 1.39 g (11.5 mmole) of N-methylbenzylamine in 20 ml of methanol for 2 days. At the end of this time, the reaction mixture was concentrated by evaporation underreduced pressure, and the residue was purified by column chromatography through silica gel (eluent: a 5: 95 by volume mixture of methanol and methylene chloride), to afford 3.13 g of the title compound as a pale brown oil.

Workup

  1. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation underreduced pressure
  2. customthe residue was purified by column chromatography through silica gel (eluent
  3. additiona 5: 95 by volume mixture of methanol and methylene chloride),

Sources & evidence

ORD record
ord-566309bff02d43ef9c7efd3b40e885c0
Source dataset
uspto-grants-1995_01
Patent number
US05378690

Reaction notes

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