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

HRID 1895004

Reaction equation

HRID 1895004 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-b8792fa57f93411fb5de3e5f50c9aa2f
Source dataset
uspto-grants-2013_08
Patent number
US08513425B2

Linked notes

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