Tetrahydrofuran → N-Benzyl-L-proline

HRID 352210Notes

Reaction equation

HRID 352210 reaction equation
C([O:3][C:4](=[O:17])[C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)C.[OH-].[Na+].O1CCCC1>CO>[CH2:10]([N:6]1[CH2:7][CH2:8][CH2:9][C@H:5]1[C:4]([OH:17])=[O:3])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 688177N-Benzyl-L-proline ethyl ester

Product 1

HCID 728719N-Benzyl-L-proline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-Benzyl-L-proline ethyl ester (1.00 g, 4.3 mmol) was combined with aqueous 2N sodium hydroxide (5.0 mL, 10.0 mmol), tetrahydrofuran (2.0 mL) and MeOH (2.0 mL) and the mixture stirred at rt. until hydrolysis was complete. The mixture was then treated in a manner similar to preparation 104. Concentration of the filtrate netted 0.79 g (90%) of crude acid as a light yellowish solid. MS(ES): (M+1)+ 206.3, 207.3.

Workup

  1. customuntil hydrolysis
  2. additionThe mixture was then treated in a manner similar to preparation 104

Sources & evidence

ORD record
ord-ad3adf203f894490af333ea0f9558871
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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