1,2-Dichloroethane → Ethyl 2-(benzylamino)propanoate

HRID 1971348Notes

Reaction equation

HRID 1971348 reaction equation
Cl.[CH2:2]([NH:4][C@H:5]([C:7]([OH:9])=[O:8])[CH3:6])[CH3:3].[CH:10](=O)[C:11]1C=C[CH:14]=[CH:13][CH:12]=1.Cl[CH2:19][CH2:20]Cl>>[CH2:19]([O:8][C:7](=[O:9])[CH:5]([NH:4][CH2:2][C:3]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:6])[CH3:20]

Participants

4

Reactant 3

HCID 111,2-DichloroethaneHCID 240BenzaldehydeHCID 86643083Ethyl alanine hydrochloride

Product 1

HCID 222273Ethyl 2-(benzylamino)propanoate

Procedure

Ethyl alanine hydrochloride (5.5 g, 36.8 mmol), benzaldehyde (7.9 mL, 77.8 mmol), TEA (10.8 mL, 77.8 mmol) and NaBH(Oac)3 (16.5 g, 77.8 mmol) are taken up in 1,2-DCE (200 mL) and stirred at rt for 4 h. The reaction is then partitioned between DCM and saturated aqueous NaHCO3. The organic layer is removed, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude residue is used without further purification. MS (ESI) m/z 208.2 (M+1).

Workup

  1. customThe reaction is then partitioned between DCM and saturated aqueous NaHCO3
  2. customThe organic layer is removed
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude residue is used without further purification

Sources & evidence

ORD record
ord-91c5d55cf2bf4f90b788b3ff63317f6b
Source dataset
uspto-grants-2013_04
Patent number
US08431584B2

Reaction notes

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