Ammonium Chloride → 4-Benzoyl-1-(3-fluoro-4-methoxyphenyl)pyrrolidin-2-one

HRID 1993385Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([N:10]2[C:14](=[O:15])[CH2:13][CH:12]([C:16](N(OC)C)=[O:17])[CH2:11]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[C:22]1([Mg]Cl)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[NH4+].[Cl-]>C1COCC1>[C:16]([CH:12]1[CH2:11][N:10]([C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([F:1])[CH:3]=2)[C:14](=[O:15])[CH2:13]1)(=[O:17])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 1-(3-fluoro-4-methoxyphenyl)-N-methoxy-N-methyl-5-oxopyrrolidine-3-carboxamide (Step 1, 2 g, 6.75 mmol) in 30 mL of THF was added 2 M phenylmagnesium chloride in THF (6.75 mL) via syringe at RT. The solution was heated to 50° C. for 2 h. The solution was poured to 50 mL of satd. NH4Cl aq. soln. The resulting mixture was extracted with 100 mL of EtOAc. The organic phase was washed with 50 mL of brine, dried over Na2SO4 and concentrated in vacuo. The crude was purified by a silica gel column chromatography (10% to 80% EtOAc/hexane) to give white solid. MS (ESI pos. ion) m/z: 314.2 (M+H). Calc'd Exact Mass for C18H16FNO3: 313.32.

Workup

additionThe solution was poured to 50 mL of satd
extractionThe resulting mixture was extracted with 100 mL of EtOAc
washThe organic phase was washed with 50 mL of brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe crude was purified by a silica gel column chromatography (10% to 80% EtOAc/hexane)
customto give white solid

Sources & evidence

ORD record: ord-dc2877a935f043a1b4c2ceba5de02f2f
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652009B2

Reaction notes

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