Water → HCID 86607428, compound

HRID 1178559Notes

Reaction equation

HRID 1178559 reaction equation
[Li][CH2:2][CH2:3][CH2:4][CH3:5].[CH:6]([C@H:8]1[CH2:12][CH2:11][C:10](=[O:13])[N:9]1[CH2:14][CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)=O.O.[CH2:27]1COCC1>CCCCCC>[CH3:5][C:4]([CH3:27])=[CH:3][CH:2]=[CH:6][C@H:8]1[CH2:12][CH2:11][C:10](=[O:13])[N:9]1[CH2:14][CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 58696435HCID 58696435, compound2×HCID 178418339Butyllithium

Product 1

HCID 86607428HCID 86607428, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a suspension of intermediate 5.1 (580 mg, 1.41 mmol) in anhydrous THF (20 mL) at −5° C. was added n-BuLi (0.97 mL, 1.6 M, 1.55 mmol) in hexane dropwise under Ar. The mixture was stirred for 20 min after addition was complete. To the reaction mixture was then added a solution of methyl 4-{2-[(2R)-2-formyl-5-oxopyrrolidin-1-yl]ethyl}benzoate (intermediate 1.4) (388 mg, 1.41 mmol) in anhydrous THF (4 mL) dropwise. The stirring was continued for 1 hr. Water was added to quench the reaction and the mixture was concentrated in vacuo to remove most of the THF. Extraction with ethyl acetate, washing organic phase with brined, drying and concentration afforded the crude product mixture containing cis and trans compounds as a pale oil, which was used directly for step without further purification.

Workup

  1. additionafter addition
  2. waitThe stirring was continued for 1 hr
  3. customto quench
  4. customthe reaction
  5. concentrationthe mixture was concentrated in vacuo
  6. customto remove most of the THF
  7. extractionExtraction with ethyl acetate
  8. washwashing organic phase with brined,
  9. customdrying
  10. concentrationconcentration

Sources & evidence

ORD record
ord-09e4d14a289a4545bb648f5e2c05d98c
Source dataset
uspto-grants-2007_10
Patent number
US07276531B2

Reaction notes

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