HCID 59540652, compound → HCID 59540819, compound

HRID 1677543Notes

Reaction equation

HRID 1677543 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:12]2[C:16](=O)[CH2:15][C:14]([CH3:19])([CH3:18])[C:13]2=O)[CH:5]=[C:6]([O:8][CH2:9][O:10][CH3:11])[CH:7]=1>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([N:12]2[CH2:16][CH2:15][C:14]([CH3:19])([CH3:18])[CH2:13]2)[CH:5]=[C:6]([O:8][CH2:9][O:10][CH3:11])[CH:7]=1

Participants

3

Reactant 1

HCID 59540652HCID 59540652, compound

Product 1

HCID 59540819HCID 59540819, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(3-bromo-5-methoxymethoxy-phenyl)-3,3-dimethyl-pyrrolidine-2,5-dione (643 mg, 1.88 mmol) in dry THF (8 ml) (under nitrogen) was added a solution of borane-dimethylsulfide complex (1.7 ml, 16.9 mmol, 10.1M) via slow drop-wise addition. The material was stirred for 12 hours. The mixture was cooled (ice bath) and carefully quenched via the slow drop-wise addition of water (10 ml). Methylene chloride (60 ml), and water (50 ml) were added and the material shaken. The organic phase was collected and washed with brine (60 ml). The aqueous phases were back extracted with methylene chloride (2×50 ml). The organics were combined, dried (MgSO4), filtered and stripped to provide a crude oil. The material was adsorbed onto silica (12 g) and purified by silica gel chromatography, eluting with 5% to 9% ethyl acetate in hexanes to afford 517 mg of 1-(3-bromo-5-methoxymethoxy-phenyl)-3,3-dimethyl-pyrrolidine as a clear oil.

Workup

  1. additionvia slow drop-wise addition
  2. temperatureThe mixture was cooled (ice bath)
  3. customcarefully quenched via the slow drop-wise addition of water (10 ml)
  4. additionMethylene chloride (60 ml), and water (50 ml) were added
  5. stirringthe material shaken
  6. customThe organic phase was collected
  7. washwashed with brine (60 ml)
  8. extractionThe aqueous phases were back extracted with methylene chloride (2×50 ml)
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customto provide a crude oil
  12. custompurified by silica gel chromatography
  13. washeluting with 5% to 9% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-9d2065c380b54c1985205a52dd4378ed
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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