(Dimethyl sulfide)trihydroboron → HCID 67406438, compound

HRID 1372617Notes

Reaction equation

HRID 1372617 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([F:13])[CH2:10][C@H:9]1[CH2:14][O:15][CH2:16][CH2:17][C:18](O)=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].CSC.B>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([F:13])[CH2:10][C@H:9]1[CH2:14][O:15][CH2:16][CH2:17][CH2:18][OH:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 67406822HCID 67406822, compound

Product 1

HCID 67406438HCID 67406438, compoundYield 120.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF (100 ml) was dissolved 3-((2S,4S)-1-(tert-butoxycarbonyl)-4-fluoro-2-pyrrolidinylmethoxy)propionic acid (2.48 g, 8.51 mmol). At room temperature, a 10.0M borane-dimethyl sulfide solution (2.79 ml, 27.9 mmol) was added and the mixture was stirred at room temperature for 3.5 hours and then, at 60° C. for 30 minutes. After cooling to room temperature, the reaction mixture was poured in ice water (100 ml), followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (silica gel: 50 g), whereby from chloroform/methanol (20/1) eluate fractions, the title compound (2.84 g, 100%) was obtained as a colorless oil.

Workup

  1. waitat 60° C. for 30 minutes
  2. temperatureAfter cooling to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was purified by chromatography on a silica gel column (silica gel: 50 g), whereby from chloroform/methanol (20/1) eluate fractions

Sources & evidence

ORD record
ord-0e90a6c8efc74e32b44b1d2f876b7f91
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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