Methanol → HCID 57516628, compound

HRID 1677553Notes

Reaction equation

HRID 1677553 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12](=O)[CH2:11][C:10]([CH3:15])([CH3:14])[C:9]2=O)[CH:5]=[CH:6][CH:7]=1.B.CO.O>C1COCC1.CSC.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][CH2:11][C:10]([CH3:15])([CH3:14])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 962WaterHCID 6331BoraneHCID 57516627HCID 57516627, compound

Product 1

HCID 57516628HCID 57516628, compoundYield 75.2%

Reagents, catalysts & solvents 3

HCID 1068Dimethyl SulfideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(3-Bromo-phenyl)-3,3-dimethyl-pyrrolidine-2,5-dione (2.5 g, 8.9 mmol) was suspended in 45 ml of THF. Borane (7.9 ml of a 10.1M solution in methyl sulfide) was added and the reaction was stirred at room temperature for 3 hours. The reaction was cooled to 0° C. in an ice bath and 20 ml of methanol was added dropwise, then 60 ml of water. The mixture was transferred to a separatory funnel and methylene chloride was added. The organic phase was washed with water and brine, filtered through celite and concentrated. The crude product was purified by flash chromatography using a gradient of 0% to 5% ethyl acetate in hexanes to give 1.7 g (75%) of 1-(3-bromo-phenyl)-3,3-dimethyl-pyrrolidine.

Workup

  1. temperatureThe reaction was cooled to 0° C. in an ice bath
  2. customThe mixture was transferred to a separatory funnel
  3. washThe organic phase was washed with water and brine
  4. filtrationfiltered through celite
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-c745c671dba54edca48666ac23551d80
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

Loading…