Water → Tert-butyl (2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidine-1-carboxylate

HRID 1920780Notes

Reaction equation

HRID 1920780 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9](OC(N2C=CN=C2)=S)[C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:5]=[CH:6][C:7]=1[CH3:8].C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N.O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[CH3:8])[CH2:9][C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 58580778Tert-butyl (2S)-2-{(3-fluoro-4-methylphenyl)[(1H-imidazol-1-yl carbonothioyl)oxy]methyl}pyrrolidine-1-carboxylate

Product 1

HCID 58581220Tert-butyl (2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidine-1-carboxylateYield 57%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Tert-butyl (2S)-2-{(3-fluoro-4-methylphenyl)[(1H-imidazol-1-yl carbonothioyl)oxy]methyl}pyrrolidine-1-carboxylate (0.83 g, 1.98 mmol), which had been obtained in Example 1 (1c), and a solution of tributyl tin hydride (1.73 g, 5.94 mmol) and 2,2′-azobis(isobutyronitrile) (0.07 g, 0.40 mmol) in toluene (4 mL) were stirred with heating under reflux for 6 hours. The reaction solution was cooled to room temperature. Water (20 mL) was added to the reaction solution, which was then extracted with ethyl acetate (20 mL×3). After that, the organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to give the title compound as a colorless oily substance (0.33 g, yield 57%).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 6 hours
  3. extractionwas then extracted with ethyl acetate (20 mL×3)
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-b7cce427d83a4e12ae1bf314716f1ae2
Source dataset
uspto-grants-2012_05
Patent number
US08173631B2

Reaction notes

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