Methanol → Methyl 1-(4-fluorophenyl)-2-oxopyrrolidine-3-carboxylate

HRID 1676319Notes

Reaction equation

HRID 1676319 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH:10]([C:13]([OH:15])=[O:14])[C:9]2=[O:16])=[CH:4][CH:3]=1.CO.[CH2:19]1COCC1.[N+](=C[Si](C)(C)C)=[N-]>CCOCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][CH2:11][CH:10]([C:13]([O:15][CH3:19])=[O:14])[C:9]2=[O:16])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 167693TrimethylsilyldiazomethaneHCID 41820071-(4-Fluorophenyl)-2-oxo-3-pyrrolidinecarboxylic acid

Product 1

HCID 67347273Methyl 1-(4-fluorophenyl)-2-oxopyrrolidine-3-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1-(4-fluorophenyl)-2-oxopyrrolidine-3-carboxylic acid (0.20 g, 0.90 mmol) in a mixture of Et2O (6 mL), MeOH (2 mL), and THF (2 mL) was added (diazomethyl)trimethylsilane (1.1 mL, 2.0 M) at 0° C. The resulting mixture was stirred for 30 minutes at room temperature, quenched with AcOH, and diluted with EtOAc. The organic layer was washed with water, NaHCO3 solution (2×), and brine, dried over MgSO4, and concentrated under reduced pressure to give the desired product (0.206 g, 98%). LRMS (ESI pos) m/e 238.0 (M+1).

Workup

  1. customquenched with AcOH
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with water, NaHCO3 solution (2×), and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0da64529774e4f90b5d51c511746a493
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

Loading…