p-Fluoronitrobenzene → HCID 21132705, compound

HRID 1645343Notes

Reaction equation

HRID 1645343 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[OH:11][C@H:12]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]1.[H-].[Na+]>C1COCC1>[C:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][C@H:12]([O:11][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:13]1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 854055tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 21132705HCID 21132705, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-Fluoronitrobenzene (2.82 g, 20 mmol) was mixed with (S)-3-hydroxy-N-Boc-pyrrolidine (3.74 g, 20 mmol) in dry THF (100 mL). At 0° C., sodium hydride (1.69 g, 60% dispensed in mineral oil, 2.20 eq) was added. The mixture was stirred at 0° C. for 60 min and at room temperature overnight. Solvents were evaporated and the residue was extracted with ethyl acetate and 0.2N hydrochloric acid. The organic layer was washed with brine and dried over sodium sulfate. After the evaporation of solvents, the residue was purified through flash column chromatography using ethyl acetate and hexanes (5% to 60% ethyl acetate) to give a crystalline material as (S)-3-(4-nitro-phenyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (4.33 g, 70.3% yield).

Workup

  1. customSolvents were evaporated
  2. extractionthe residue was extracted with ethyl acetate and 0.2N hydrochloric acid
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customAfter the evaporation of solvents
  6. customthe residue was purified through flash column chromatography

Sources & evidence

ORD record
ord-8ef305f638c54f7d96a14baf026fe08b
Source dataset
uspto-grants-2012_02
Patent number
US08124766B2

Reaction notes

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