N-Fluorobenzenesulfonimide → HCID 22241213, compound

HRID 1883596Notes

Reaction equation

HRID 1883596 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[O:26])[N:7]([CH:14]1[CH2:19][CH:18]([O:20][C:21](=[O:23])[CH3:22])[C:17](=[O:24])[NH:16][C:15]1=[O:25])[C:8]2=[O:13])([O-:3])=[O:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:47])(=O)=O)=CC=1>O1CCCC1>[F:47][C:14]1([N:7]2[C:6](=[O:26])[C:5]3[C:9](=[CH:10][CH:11]=[CH:12][C:4]=3[N+:1]([O-:3])=[O:2])[C:8]2=[O:13])[CH2:19][CH:18]([O:20][C:21](=[O:23])[CH3:22])[C:17](=[O:24])[NH:16][C:15]1=[O:25]

Participants

5

Reactant 3

HCID 588007N-FluorobenzenesulfonimideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 22241217HCID 22241217, compound

Product 1

HCID 22241213HCID 22241213, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 1-tert-butoxycarbonyl]-3-(4-nitro-1,3-dioxoisoindolin-2-yl)-2,6-dioxo-5-acetoxypiperidine (2.0 g, 4.3 mmol) in tetrahydrofuran (20 mL) is added sodium bis(trimethylsilyl)amide (4.3 mL, 4.3 mmol, 1.0 M) in tetrahydrofuran at −78° C. After 10-30 minutes, N-fluorobenzenesulfonimide (1.1 g, 4.3 mmol) is added to the mixture. The mixture is warmed to room temperature and the solvent is removed in vacuo. The residue is stirred with ethyl acetate (10 mL) and hydrochloric acid (10 mL, 1N) for 1 hour, the organic layer is separated, and the solvent is removed in vacuo to give 3-fluoro-3-(4-nitro-1,3-dioxoisoindolin-2-yl)-2,6-dioxo-5-acetoxypiperidine which is further purified by column chromatography.

Workup

  1. customthe solvent is removed in vacuo
  2. customthe organic layer is separated
  3. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-06d099b95e424972997c448d0ac96fdf
Source dataset
uspto-grants-2004_07
Patent number
US06762195B2

Reaction notes

Loading…