alpha,alpha-Dimethyl-2-naphthaleneethanamine → Methyl 3-[2-[(1R)-1-[(2R)-2-hydroxy-3-[[2-methyl-1-(naphthalen-2-yl)propan-2-yl]amino]propoxy]ethyl]phenyl]propionate

HRID 1181588Notes

Reaction equation

HRID 1181588 reaction equation
[O:1]1[CH2:3][C@@H:2]1[CH2:4][O:5][C@@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH3:7].[CH3:20][C:21]([NH2:34])([CH3:33])[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1.Cl([O-])(=O)(=O)=O.[Li+]>C(#N)C>[OH:1][C@H:2]([CH2:3][NH:34][C:21]([CH3:33])([CH3:20])[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)[CH2:4][O:5][C@@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH3:7]

Participants

5

Reactant 3

HCID 15369616alpha,alpha-Dimethyl-2-naphthaleneethanamineHCID 23665649Lithium perchlorateHCID 58662605methyl 3-[2-[(1R)-1-(((2R)-oxiranyl)methoxy)ethyl]phenyl]propionate

Product 1

HCID 58662623Methyl 3-[2-[(1R)-1-[(2R)-2-hydroxy-3-[[2-methyl-1-(naphthalen-2-yl)propan-2-yl]amino]propoxy]ethyl]phenyl]propionateYield 107.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 3-[2-[(1R)-1-(((2R)-oxiranyl)methoxy)ethyl]phenyl]propionate (286 mg) obtained in Step 3 was dissolved in acetonitrile (10 ml), [2-methyl-1-(naphthalen-2-yl)propan-2-yl]amine (218 mg) and lithium perchlorate (157 mg) were successively added, and the mixture was heated under reflux overnight. The reaction mixture was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to give the title compound (539 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-05c148326ee949cd9807edd75191c042
Source dataset
uspto-grants-2007_10
Patent number
US07285572B2

Reaction notes

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