Dimethyl Sulfide → HCID 59505672, compound

HRID 1253642Notes

Reaction equation

HRID 1253642 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([NH:5][C@H:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=2)[CH2:8][CH2:7]1)=O.S(C)C>C1COCC1>[F:1][C:2]([F:19])([F:20])[CH2:3][NH:5][C@H:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=2)[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 59505312HCID 59505312, compound

Product 1

HCID 59505672HCID 59505672, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of (R)-methyl 3-(2,2,2-trifluoroacetamido)-2,3-dihydro-1H-indene-5-carboxylate (1.8 g, 6.27 mmol, 1.0 eq.) in THF (30 ml) is added BH3.Me2S (0.9 ml, 9.4 mmol, 1.5 eq.) drop wise and the reaction mixture is heated at reflux for 2 h. The reaction mixture is then quenched with MeOH (0.5 ml) and then partitioned between water (30 ml) and ethyl acetate (100 ml). The organic layer is washed with brine (30 ml), dried over anhydrous Na2SO4 and evaporated to get the crude which is purified by column chromatography (silica gel; 4% ethyl acetate/hexanes) to yield the desired compound as a colourless oil. Yield: 43% (730 mg, 2.67 mmol).

Workup

  1. additionis added BH3
  2. temperatureat reflux for 2 h
  3. customThe reaction mixture is then quenched with MeOH (0.5 ml)
  4. custompartitioned between water (30 ml) and ethyl acetate (100 ml)
  5. washThe organic layer is washed with brine (30 ml)
  6. dry with materialdried over anhydrous Na2SO4
  7. customevaporated
  8. customto get the crude which
  9. customis purified by column chromatography (silica gel; 4% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-86874e975d3243519fcedeb8160485f3
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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