alpha,alpha-Dimethyl-2-naphthaleneethanamine → Ethyl 5-[2-[1-[(2R)-2-hydroxy-3-[[2-methyl-1-(naphthalen-2-yl)propan-2-yl]amino]propoxy]ethyl]phenyl]thiophene-2-carboxylate

HRID 1181603Notes

Reaction equation

HRID 1181603 reaction equation
[O:1]1[CH2:3][C@@H:2]1[CH2:4][O:5][CH:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[S:18][C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:16][CH:15]=1)[CH3:7].[CH3:24][C:25]([NH2:38])([CH3:37])[CH2:26][C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=1.Cl([O-])(=O)(=O)=O.[Li+]>C1(C)C=CC=CC=1>[OH:1][C@H:2]([CH2:3][NH:38][C:25]([CH3:37])([CH3:24])[CH2:26][C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=1)[CH2:4][O:5][CH:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[S:18][C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:16][CH:15]=1)[CH3:7]

Participants

5

Reactant 3

HCID 15369616alpha,alpha-Dimethyl-2-naphthaleneethanamineHCID 23665649Lithium perchlorateHCID 58662606Ethyl 5-[2-[1-(((2R)-oxiranyl)methoxy)ethyl]phenyl]thiophene-2-carboxylate

Product 1

HCID 58662609Ethyl 5-[2-[1-[(2R)-2-hydroxy-3-[[2-methyl-1-(naphthalen-2-yl)propan-2-yl]amino]propoxy]ethyl]phenyl]thiophene-2-carboxylateYield 96.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 5-[2-[1-(((2R)-oxiranyl)methoxy)ethyl]phenyl]thiophene-2-carboxylate (499 mg) obtained in Step 4 was dissolved in toluene, [2-methyl-1-(naphthalen-2-yl)propan-2-yl]amine (299 mg) and lithium perchlorate (160 mg) were successively added, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=30:1) to give the title compound (770 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-bb7a154918ab43ca84190124fac0239f
Source dataset
uspto-grants-2007_10
Patent number
US07285572B2

Reaction notes

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