Bromoform → HCID 11773244, compound

HRID 1814028Notes

Reaction equation

HRID 1814028 reaction equation
[CH:1]([Br:4])(Br)[Br:2].[N:5]1([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:9][CH:8]=[CH:7][CH2:6]1>ClCCl.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[CH2:13]([O:12][C:10]([N:5]1[CH2:9][CH:8]2[CH:7]([C:1]2([Br:4])[Br:2])[CH2:6]1)=[O:11])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 2

HCID 5558BromoformHCID 643471Benzyl 3-pyrroline-1-carboxylate

Product 1

HCID 11773244HCID 11773244, compound

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

A solution of bromoform (0.94 mL, 10.8 mmol) in 5 mL of dichloromethane was added over 1.5 hours to a stirred solution of benzyl 3-pyrroline-1-carboxylate (1.77 mL, 9.8 mmol) and benzyltriethylammonium chloride (0.055 g, 0.025 mmol) in 1:1 dichloromethane-50% aqueous NaOH (60 mL). The black solution was stirred for 18 hours at room temperature and then diluted with dichloromethane and H2O. The layers were separated and the organic phase washed with satd NH4Cl, brine, and dried (MgSO4), filtered and concentrated. The crude product was purified by column chromatography (0-20% ethyl acetate-hexane) to afford 6,6-dibromo-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester.

Workup

  1. customThe layers were separated
  2. washthe organic phase washed with satd NH4Cl, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (0-20% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-4d6b250d35904ca3a560bcd51415ec39
Source dataset
uspto-grants-2005_04
Patent number
US06875784B2

Reaction notes

Loading…