Sodium hydride → (2R)-1-[6-(Cyclopropylmethoxy)-1-fluoro-2-naphthyloxy]-4-(3-pyridyl)-2-butanol

HRID 1600993Notes

Reaction equation

HRID 1600993 reaction equation
C1(C)C=CC(S([O:10][CH2:11][C@H:12]([O:21][Si](C(C)(C)C)(C)C)[CH2:13][CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)(=O)=O)=CC=1.[H-].[Na+].[CH:32]1([CH2:35][O:36][C:37]2[CH:38]=[C:39]3[C:44](=[CH:45][CH:46]=2)[C:43]([F:47])=[C:42](O)[CH:41]=[CH:40]3)[CH2:34][CH2:33]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O.O1CCCC1.O>[CH:32]1([CH2:35][O:36][C:37]2[CH:38]=[C:39]3[C:44](=[CH:45][CH:46]=2)[C:43]([F:47])=[C:42]([O:10][CH2:11][C@H:12]([OH:21])[CH2:13][CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:41]=[CH:40]3)[CH2:33][CH2:34]1

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 2724141Tetrabutylammonium FluorideHCID 218306366-(Cyclopropylmethoxy)-1-fluoronaphthalen-2-olHCID 54162583(2R)-2-(tert-butyldimethylsilyloxy)-4-(3-pyridyl)-1-butyl para-toluenesulfonate

Product 1

HCID 54564888(2R)-1-[6-(Cyclopropylmethoxy)-1-fluoro-2-naphthyloxy]-4-(3-pyridyl)-2-butanolYield 40.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Prepared according to the method described in Example 26e) from (2R)-2-(tert-butyldimethylsilyloxy)-4-(3-pyridyl)-1-butyl para-toluenesulfonate (0.215 g), sodium hydride (60% dispersion in mineral oil, 0.02 g) and 6-cyclopropylmethoxy-1-fluoro-2-hydroxynaphthalene (0.115 g) in dimethylformamide (3 ml). The adduct was dissolved in tetrahydrofuran (5 ml) and tetrabutylammonium fluoride (0.25 g) was added. The reaction was stirred at room temperature for 2 hours and was then poured into water and extracted with ethyl acetate. The organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography eluting with acetone:hexane (2:3) to give the title compound as a solid (0.077 g).

Workup

  1. customPrepared
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography
  7. washeluting with acetone:hexane (2:3)

Sources & evidence

ORD record
ord-8b62a82cdfc2467cb9f71eb2dd5b5ffa
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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