Dimethylamine → (S)-ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3-((dimethyl-amino)methyl)naphthalen-2-yl)acetate

HRID 514021Notes

Reaction equation

HRID 514021 reaction equation
Br[CH2:2][C:3]1[C:4]([C@H:20]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:5]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.[CH3:31][NH:32][CH3:33]>C1COCC1>[C:27]([O:26][C@@H:20]([C:4]1[C:3]([CH2:2][N:32]([CH3:33])[CH3:31])=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22])([CH3:28])([CH3:29])[CH3:30]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 68085819(S)-ethyl 2-(3-(bromomethyl)-1-(4-chlorophenyl)naphthalen-2-yl)-2-tert-butoxyacetate

Product 1

HCID 68086084(S)-ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3-((dimethyl-amino)methyl)naphthalen-2-yl)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-ethyl 2-(3-(bromomethyl)-1-(4-chlorophenyl)naphthalen-2-yl)-2-tert-butoxyacetate (12 mg, 0.0245 mmol) in THF (1 mL) was added dimethylamine (2 M in THF, 0.12 μL). The reaction mixture was stirred at room temperature for 1 h. Removal of the solvent in vacuo followed by purification of the residue by flash chromatography (silica gel, ethyl acetate/hexanes) provided 8 mg of the desired product. LCMS-ESI+ (m/z): [M+H]+ calcd for C27H33ClNO3: 454.2. Found: 454.2, 456.1.

Workup

  1. customRemoval of the solvent in vacuo
  2. customfollowed by purification of the residue by flash chromatography (silica gel, ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-c656164b76554c5d9c1a86d44dded02d
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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