Boron trifluoride etherate → 3-Formyl-3-phenyl-pyrrolidine-1-carboxylic acid methyl ester

HRID 661528Notes

Reaction equation

HRID 661528 reaction equation
B(F)(F)F.CCOCC.[CH3:10][O:11][C:12]([N:14]1[CH2:20][CH2:19][C:18]2([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:16]([O:17]2)[CH2:15]1)=[O:13]>>[CH3:10][O:11][C:12]([N:14]1[CH2:20][CH2:19][C:18]([CH:16]=[O:17])([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:15]1)=[O:13]

Participants

3

Reactant 2

HCID 8000Boron trifluoride etherateHCID 58017280HCID 58017280, compound

Product 1

HCID 580172733-Formyl-3-phenyl-pyrrolidine-1-carboxylic acid methyl esterYield 97.1%

Procedure

Boron trifluoride diethyl etherate (1.82 mL, 14.40 mmol) was slowly added at room temperature to a solution of 6-phenyl-7-oxa-3-aza-bicyclo[4.1.0]heptane-3-carboxylic acid methyl ester (1.68 g, 7.20 mmol). A slightly exothermic reaction was observed and after 5 minutes the reaction mixture was quenched by slow addition of saturated aqueous NaHCO3 (50 mL). The resulting mixture was extracted with EtOAc, and the combined organic extracts were washed with water, dried over MgSO4, filtered and evaporated under reduced pressure to give 1.63 g (97% yield) of 3-formyl-3-phenyl-pyrrolidine-1-carboxylic acid methyl ester as a pale yellow oil which was used without further purification.

Workup

  1. customA slightly exothermic reaction
  2. customthe reaction mixture was quenched by slow addition of saturated aqueous NaHCO3 (50 mL)
  3. extractionThe resulting mixture was extracted with EtOAc
  4. washthe combined organic extracts were washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a38dab67055042998d9fe456f015a8d8
Source dataset
uspto-grants-2011_12
Patent number
US08084623B2

Reaction notes

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