Benzaldehyde → N-Benzyl-L-proline ethyl ester

HRID 1253495Notes

Reaction equation

HRID 1253495 reaction equation
[NH:1]1[CH2:10][CH2:9][CH2:8][C@H:2]1[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>ClCCl.C(O)(=O)C>[CH2:11]([N:1]1[CH2:10][CH2:9][CH2:8][C@H:2]1[C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 11430Potassium CarbonateHCID 79888L-Proline, ethyl esterHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 688177N-Benzyl-L-proline ethyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Into a 500 ml 3-necked roundbottom flask, was placed ethyl prolinate (20.0 g, 140. mmol). This was followed by the addition of a solution of benzaldehyde (14.8 g, 140. mmol) in dichloromethane (100 ml). This was followed by the addition of a solution of sodium triacetoxyborohydride (60.0 g, 280. mmol) in acetic acid (20 ml). The resulting solution was allowed to stirring for 12 hours at room temperature. Adjustment of the pH to 7 was accomplished by the addition of solid potassium carbonate. The resulting solution was extracted one time with 500 ml of EtOAc and concentrated by evaporation to afford ethyl 1-benzylprolinate that was used without further purification.

Workup

  1. customInto a 500 ml 3-necked roundbottom flask, was placed
  2. extractionThe resulting solution was extracted one time with 500 ml of EtOAc
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-d3d50646bb3147cdb6c510194095da9a
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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