Hydrochloric Acid → N-Benzyl-L-proline

HRID 467948Notes

Reaction equation

HRID 467948 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[OH-].[K+].[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>C(O)(C)C>[CH2:11]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 14797Potassium HydroxideHCID 145742L-Proline

Product 1

HCID 728719N-Benzyl-L-proline

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 10 g of L-proline and KOH (10 g) in 120 mL isopropanol was stirred at 40° C., then benzyl chloride (13.5 mL) was added dropwise. The reaction mixture was stirred for 6 additional hours, then neutralized with concentrated HCl to a pH of 5-6. The reaction mixture was extracted with CH2Cl2 (3×70 mL), the combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, the solids were removed by filtration and the solvents of the filtrate were removed under reduced pressure. The residue was treated with acetone to afford N-benzyl proline (15 g).

Workup

  1. extractionThe reaction mixture was extracted with CH2Cl2 (3×70 mL)
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solids were removed by filtration
  5. customthe solvents of the filtrate were removed under reduced pressure
  6. additionThe residue was treated with acetone

Sources & evidence

ORD record
ord-d8bcad2317644e6fbbeecf932bd27ae2
Source dataset
uspto-grants-2014_01
Patent number
US08623899B2

Reaction notes

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