Hydrochloric Acid → 1-Benzyl-L-proline hydrochloride

HRID 1366641Notes

Reaction equation

HRID 1366641 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:17][CH2:16][CH2:15][C@H:9]2[C:10]([O:12]CC)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[ClH:20]>C1COCC1.CCO.O>[ClH:20].[C:1]1([CH2:7][N:8]2[CH2:17][CH2:16][CH2:15][C@H:9]2[C:10]([OH:12])=[O:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 688177N-Benzyl-L-proline ethyl ester

Product 1

HCID 573677341-Benzyl-L-proline hydrochlorideYield 97%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1-(phenylmethyl)-L-prolinate (13.20 g, 56.57 mmol) was dissolved in a mixture of THF (40 mL), EtOH (40 mL) and H2O (16 mL). To this solution was added solid sodium hydroxide (6.789 g, 169.73 mmol), and the mixture was stirred at room temperature overnight. The solution was adjusted to pH 2 with 1N aq. HCl and then extracted with CH2Cl2 (3×50 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo, and the resulting crude product was 1-(phenylmethyl)-L-proline hydrochloride (0.8 g). The aqueous layers were concentrated in vacuo, the residue was suspended in MeOH, and the resulting solid precipitate was collected by filtration and combined with the product from the organic extracts to provide 1-(phenylmethyl)-L-proline hydrochloride (13.30 g, 97%). LCMS: (M+H)+: 206.1

Workup

  1. extractionextracted with CH2Cl2 (3×50 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. concentrationThe aqueous layers were concentrated in vacuo
  6. filtrationthe resulting solid precipitate was collected by filtration

Sources & evidence

ORD record
ord-fd41e1b8656c4407b929bbfe4b1de994
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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