proline dl-form → Benzyl 1-benzylprolinate

HRID 1669446Notes

Reaction equation

HRID 1669446 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[NH:15]1[CH2:22][CH2:21][CH2:20][CH:16]1[C:17]([OH:19])=[O:18]>CN(C=O)C.CCOC(C)=O>[CH2:1]([N:15]1[CH2:22][CH2:21][CH2:20][C@H:16]1[C:17]([O:19][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 614proline dl-formHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 11781411Benzyl 1-benzylprolinateYield 43%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Benzyl bromide (2 eq.) and K2CO3 (2.5 eq) were added to a solution (0.6 M) of DL-proline in DMF. The reaction was stirred at 100° C. overnight. The solution was allowed to cool to RT and then diluted with EtOAc and washed with 1 N HCl, brine, before being dried (Na2SO4), filtered and concentrated in vacuo. The crude material was purified by FC (PE/EtOAc 90:10) to afford the product (43%). (ES+) m/z 296 (M+H)+

Workup

  1. temperatureto cool to RT
  2. washwashed with 1 N HCl, brine
  3. dry with materialbefore being dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by FC (PE/EtOAc 90:10)

Sources & evidence

ORD record
ord-240f1b1bfc184609a441d76755ab419f
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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