1-Fluoro-3-nitrobenzene → HCID 58154811, compound

HRID 2102483Notes

Reaction equation

HRID 2102483 reaction equation
[H-].[Na+].[C:3]([N:10]1[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11]1)([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].F[C:17]1[CH:18]=[C:19]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:21][CH:22]=1>CS(C)=O>[C:6]([O:5][C:3]([N:10]1[CH2:14][CH2:13][CH:12]([O:15][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)[CH2:11]1)=[O:4])([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 98231-Fluoro-3-nitrobenzeneHCID 24758Sodium hydrideHCID 854055tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 58154811HCID 58154811, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of NaH (0.17 g, 4.4 mmol, 1.1 equiv) in DMSO (4 mL) at rt was added (3S)-1-Boc-3-pyrrolidinol (0.75 g, 4.0 mmol, 1.00 equiv) in one portion. After stirring for 20 min, 3-fluoronitrobenzene (0.51 g, 3.6 mmol, 0.90 equiv) was added drop wise and the resulting suspension was stirred an additional 1.5 hours at rt. The reaction mixture was quenched with the addition of saturated, aqueous NH4Cl and extracted with ethyl acetate (3×). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated. Purification of the crude residue by chromatography (30% ethyl acetate in hexanes) afforded 3-(3-nitro-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester as a bright yellow oil (0.676 g, 60%).

Workup

  1. stirringthe resulting suspension was stirred an additional 1.5 hours at rt
  2. customThe reaction mixture was quenched with the addition of saturated, aqueous NH4Cl
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification of the crude residue by chromatography (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-b29e7b9dba63479c8fc261efac617545
Source dataset
uspto-grants-2009_08
Patent number
US07576085B2

Reaction notes

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