1-(1,1-Dimethylethyl) 2-ethyl (2S)-5-oxo-1,2-pyrrolidinedicarboxylate → (S)-2-tert-Butoxycarbonylamino-5-oxo-hexanoic acid ethyl ester

HRID 45587Notes

Reaction equation

HRID 45587 reaction equation
[O:1]=[C:2]1[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:4][CH2:3]1.O.[C:20](=O)(O)[O-].[Na+]>O1CCCC1>[CH2:17]([O:16][C:14](=[O:15])[C@@H:5]([NH:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4][CH2:3][C:2](=[O:1])[CH3:20])[CH3:18]

Participants

4

Reactant 2

HCID 54611861-(1,1-Dimethylethyl) 2-ethyl (2S)-5-oxo-1,2-pyrrolidinedicarboxylateHCID 86585896Sodium bicarbonate water

Product 1

HCID 58544329(S)-2-tert-Butoxycarbonylamino-5-oxo-hexanoic acid ethyl esterYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-1-tert-butyl 2-ethyl 5-oxopyrrolidine-1,2-dicarboxylate (7.00 g, 27.4 mmol) in tetrahydrofuran (100 mL) was added methyl Grignard reagent (3M in diethyl ether, 9.60 mL, 28.8 mmol) dropwise for 20 minutes at −78° C., and stirred for 1 hour. After stiffing for 2 hours at 0° C., to the mixture was added saturated sodium bicarbonate water dropwise, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to give the title compound (7.60 g, 26.5 mmol, 97%).

Workup

  1. waitAfter stiffing for 2 hours at 0° C., to the mixture
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-974ac14126504f90a5b89d96629da190
Source dataset
uspto-grants-2013_09
Patent number
US08541585B2

Reaction notes

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