N-Fluorobenzenesulfonimide → HCID 22241213, compound

HRID 891998Notes

Reaction equation

HRID 891998 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. waitAfter 10–30 minutes
  2. customthe solvent is removed in vacuo
  3. customthe organic layer is separated
  4. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-ccd857075d844d9ea33eb6f0cc3653f0
Source dataset
uspto-grants-2006_02
Patent number
US07005438B2

Reaction notes

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