HCID 86629197, compound → HCID 57650043, compound

HRID 2063493Notes

Reaction equation

HRID 2063493 reaction equation
C(=[C:3]([C:21](=[O:23])[CH3:22])[C:4]([C@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:5])=O>C(O)(C(F)(F)F)=O.ClCCl>[O:23]=[C:21]([CH3:22])[CH2:3][C:4]([C@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])=[O:5]

Participants

4

Reactant 1

HCID 86629197HCID 86629197, compound

Product 1

HCID 57650043HCID 57650043, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (2R)-benzyl 2-(2-(carbonyl)-3-oxobutanoyl)pyrrolidine-1-carboxylate in TFA (50 mL) and dichloromethane (50 mL) was stirred at room temperature for 1 hr and then concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (hexanes/ethyl acetate gradient, 10-100% EtOAc) to afford (R)-benzyl 2-(3-oxobutanoyl)pyrrolidine-1-carboxylate (2.1 g, 18% over two steps). LCMS: 6.9 min calculated: 289, found (MH+): 290.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resulting residue was purified by silica gel column chromatography (hexanes/ethyl acetate gradient, 10-100% EtOAc)

Sources & evidence

ORD record
ord-e8c54207e5b244b39411bc728462a267
Source dataset
uspto-grants-2012_10
Patent number
US08288371B2

Reaction notes

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