Sodium Iodide → Dibenzyl (S)-2,5-dihydro-1H-pyrrole-1,2-dicarboxylate

HRID 1052118Notes

Reaction equation

HRID 1052118 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]=[CH:13][C@H:12]1[C:16]([OH:18])=[O:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[I-].[Na+]>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]=[CH:13][C@H:12]1[C:16]([O:18][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:17])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 10422063(S)-2,5-Dihydro-pyrrole-1,2-dicarboxylic acid 1-benzyl ester

Product 1

HCID 11142303Dibenzyl (S)-2,5-dihydro-1H-pyrrole-1,2-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid 1-benzyl ester (29.6 g, 120 mmol) in DMF (250 mL) were added cesium carbonate (42.9 g, 132 mmol) followed by benzyl bromide (17.09 mL, 144 mmol) and sodium iodide (2.15 g, 14.37 mmol) and the mixture was stirred at RT for 48 h. The reaction mixture was quenched with water (500 mL) and extracted with EtOAc (3×200 mL). The organic extracts were combined and washed with brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc 4:1) to give the desired material. MS (UPLC/MS): 338 [MH-Boc]+; tR (HPLC conditions b): 2.31 min.

Workup

  1. customThe reaction mixture was quenched with water (500 mL)
  2. extractionextracted with EtOAc (3×200 mL)
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-b35c9226983948cfa02c054a65a95f7e
Source dataset
uspto-grants-2016_07
Patent number
US09388199B2

Reaction notes

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