Water → Methyl 3-(2-aminoethyl)benzoate

HRID 587929Notes

Reaction equation

HRID 587929 reaction equation
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])#[N:2].[BH4-].[Na+].FC(F)(F)C(O)=O.O>C1COCC1>[NH2:2][CH2:1][CH2:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 10821136Methyl 3-(cyanomethyl)benzoate

Product 1

HCID 10511548Methyl 3-(2-aminoethyl)benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 1.31 g (7.48 mmol) of methyl 3-(cyanomethyl)benzoate in 31 mL of THF stirred at −10° C. was slowly added 710 mg (18.7 mmol) of sodium borohydride followed by 1.44 mL (18.7 mmol) of trifluoroacetic acid. The mixture was warmed to 22° C. and stirred for about 16 h. About 100 mL of water was carefully added to the mixture (gas evolution). The mixture was extracted with ethyl acetate (5×50 mL). The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to give methyl 3-(2-aminoethyl)benzoate which was used in the next step without purification.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (5×50 mL)
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-31e5b19b304849e6917c986081a11aa4
Source dataset
uspto-grants-2016_01
Patent number
US09227918B2

Reaction notes

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