Tert-butyl 3-oxopyrrolidine-1-carboxylate → HCID 59170230, compound

HRID 1446338Notes

Reaction equation

HRID 1446338 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[O:10]=[C:11]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]1>C(OCC)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:11]2([OH:10])[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:12]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 178418676HCID 178418676, compound

Product 1

HCID 59170230HCID 59170230, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4-fluorophenylmagnesium bromide (1M in THF, 11 mL, 11 mmol) was added gradually to a solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (1.85 g, 10 mmol) in diethyl ether (40 mL) during 5 min at ambient temperature. The mixture was stirred for 30 min and thereafter slowly quenched with NH3Cl (10 mL, 3M). The organic phase was isolated and evaporated. The residue was purified by flash chromatography (SiO2 2:1 heptane/EtOAc) to afford the title compound, which was used without further purification. MS (EI) 208 (M-tBuO)

Workup

  1. customslowly quenched with NH3Cl (10 mL, 3M)
  2. customThe organic phase was isolated
  3. customevaporated
  4. customThe residue was purified by flash chromatography (SiO2 2:1 heptane/EtOAc)

Sources & evidence

ORD record
ord-bc23e03fe9c64d1a9e07eb9f652a263d
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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