Tetrahydrofuran → HCID 58580717, compound

HRID 1920798Notes

Reaction equation

HRID 1920798 reaction equation
[Si:1]([O:8][C@@H:9]([CH2:25][O:26][C@@H:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH:35]=[CH2:36])[CH3:28])[CH2:10][N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([F:24])[CH:18]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C12BC(CCC1)CCC2.[O:46]1CCCC1>O>[Si:1]([O:8][C@H:9]([CH2:10][N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([F:24])[CH:18]=1)[CH2:25][O:26][C@@H:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35][CH2:36][OH:46])[CH3:28])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 789669-Borabicyclo(3.3.1)nonaneHCID 58580729HCID 58580729, compound

Product 1

HCID 58580717HCID 58580717, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(2S)-1-{(2R)-2-{[Tert-butyl(dimethyl)silyl]oxy}-3-[(1R)-1-(2-ethenylphenyl)ethoxy]propyl}-2-(3-fluoro-4-methylbenzyl)pyrrolidine (1.20 g, 2.35 mmol), which had been obtained in Example 180 (180c), was dissolved in tetrahydrofuran (20 mL) and added with a 0.5 M solution of 9-borabicyclo[3,3,1]nonane in tetrahydrofuran (5.6 mL, 2.82 mmol). After raising the temperature to room temperature, the mixture was stirred for 16 hours. Separately, the reaction solution was added dropwise in small portions to a solution in which sodium perborate hydrate (1.40 g, 14 mmol) was dissolved in water (20 mL), and the resulting mixture was stirred at room temperature for 2 hours. The reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by basic silica gel chromatography (n-hexane/ethyl acetate=3/1) to give the title compound as a colorless oily substance (1.05 g, yield 84%).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 2 hours
  2. extractionThe reaction solution was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by basic silica gel chromatography (n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-fa8bfec36d834dbda6019965f8fb70f1
Source dataset
uspto-grants-2012_05
Patent number
US08173631B2

Reaction notes

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