Methanol → HCID 57516628, compound

HRID 1898576Notes

Reaction equation

HRID 1898576 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.CO.O.C(Cl)Cl>C1COCC1>[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

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 6344DichloromethaneHCID 57516627HCID 57516627, compound

Product 1

HCID 57516628HCID 57516628, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(3-Bromophenyl)-3,3-dimethyl-pyrrolidine-2,5-dione (10.6 g, 37.7 mmol) was suspended in 200 ml of THF. Borane dimethyl sulfide complex (33 ml of a 10.1 M solution) was added and the reaction was stirred at room temperature for 3 hrs. The reaction was cooled in an ice bath. Methanol (100 ml) was added dropwise, followed by 300 ml of water. This mixture was transferred to a separatory funnel and DCM was added. The organic phase was isolated, washed with brine, filtered through Celite and concentrated. The product was chromatographed using a gradient of 0% to 5% ethyl acetate in hexanes, concentrated, triturated with methanol and filtered to give 8.0 g (84%) of 1-(3-bromophenyl)-3,3-dimethyl-pyrrolidine.

Workup

  1. temperatureThe reaction was cooled in an ice bath
  2. customThis mixture was transferred to a separatory funnel
  3. customThe organic phase was isolated
  4. washwashed with brine
  5. filtrationfiltered through Celite
  6. concentrationconcentrated
  7. customThe product was chromatographed
  8. concentrationconcentrated
  9. customtriturated with methanol
  10. filtrationfiltered

Sources & evidence

ORD record
ord-a92e53d949584bf589cdcab1dc3b6fc2
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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