Tetrahydrofuran → HCID 86602285, compound

HRID 2275634Notes

Reaction equation

HRID 2275634 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:9]=[C:10]1[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:12]([C:22]([O:24][CH3:25])=[O:23])[CH2:11]1.O1CCCC1>CCOCC>[OH:9][C:10]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[C@H:12]([C:22]([O:24][CH3:25])=[O:23])[CH2:11]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 109884851-tert-butyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylateHCID 178418255HCID 178418255, compound

Product 1

HCID 86602285HCID 86602285, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Phenylmagnesium bromide in ether (3.00M, 0.400 mL) was added to a solution of 1-tert-butyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylate (243.0 mg, 0.0009989 mol) in tetrahydrofuran (5.00 mL, 0.0616 mol) at −40° C. The reaction mixture was stirred at between −40° C. and −10° C. for 2 h and then was quenched with ammonium chloride solution (5 mL). The organic phase was separated and the aqueous phase was extracted with ethyl acetate (2×5 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was used directly in the next step without further purification.

Workup

  1. customwas quenched with ammonium chloride solution (5 mL)
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted with ethyl acetate (2×5 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was used directly in the next step without further purification

Sources & evidence

ORD record
ord-ed45c48c9c9d49feb42443e90269927a
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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