Methanol → methyl 3-(1E)-(4-(3-(cyclopropylamino)-2-(4-fluorophenyl) prop-1-en-1-yl)phenyl)acrylate

HRID 2098569Notes

Reaction equation

HRID 2098569 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[CH2:22]O)=[CH:9]\[C:10]2[CH:15]=[CH:14][C:13]([CH:16]=[CH:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[CH:24]1([NH2:27])[CH2:26][CH2:25]1.CO.[BH4-].[Na+]>C(OCC)(=O)C>[CH:24]1([NH:27][CH2:22]/[C:8](/[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:9]/[C:10]2[CH:15]=[CH:14][C:13]([CH:16]=[CH:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=2)[CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 887MethanolHCID 69828CyclopropylamineHCID 4311764Sodium borohydrideHCID 68768999methyl 3-(1E)(4-(2-(4-fluorophenyl)-3-hydroxyprop-1-en-1-yl)phenyl)acrylate

Product 1

HCID 68768910methyl 3-(1E)-(4-(3-(cyclopropylamino)-2-(4-fluorophenyl) prop-1-en-1-yl)phenyl)acrylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 3-(1E)(4-(2-(4-fluorophenyl)-3-hydroxyprop-1-en-1-yl)phenyl)acrylate (0.44 g, 1.4 mmol) and cyclopropylamine (0.14 g, 2.4 mmol) was stirred with MeOH (40 mL) for 3 hours. To the reaction mixture, sodium borohydride (0.09 g, 2.3 mmol) was added and stirred for 30 minutes. Subsequently the reaction mixture was diluted with ethyl acetate (300 mL) and washed successively with water (2×100 ml) and brine (1×100 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to afford the pure title compound as a pale yellow sticky compound (0.4 g, 80% yield).

Workup

  1. washwashed successively with water (2×100 ml) and brine (1×100 mL)
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d72aaa9290ac48bba8f3a32516c03f27
Source dataset
uspto-grants-2013_05
Patent number
US08450525B2

Reaction notes

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