Sodium sulfate decahydrate → HCID 67583583, compound

HRID 1456549Notes

Reaction equation

HRID 1456549 reaction equation
C(O[C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si](C(C)(C)C)(C)C)[CH2:10][C@H:9]1[CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].[H-]>O1CCCC1>[F:30][C:27]1[CH:28]=[CH:29][C:24]([O:23][CH2:22][CH2:21][C@@H:9]2[CH2:10][C@@H:11]([OH:13])[CH2:12][N:8]2[CH3:6])=[C:25]([CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)[CH:26]=1

Participants

6

Reactant 4

HCID 62649Sodium sulfate decahydrateHCID 166653HydrideHCID 21226445Aluminium lithium hydrideHCID 67584017HCID 67584017, compound

Product 1

HCID 67583583HCID 67583583, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

398 mg of (2R,4R)-1-t-butoxycarbonyl-4-t-butyldimethylsilyloxy-2-[2-{4-fluoro-2-[2-(4-fluorophenyl)ethyl]phenoxy}ethyl]pyrrolidine [prepared as described in step (a) above] were dissolved in 10 ml of tetrahydrofiran, and the resulting solution was added dropwise to a suspension of 81 mg of lithium aluminum hydride in 10 ml of tetrahydrofuran, whilst ice-cooling and stirring. The resulting mixture was then heated under reflux for 1 hour. At the end of this time, the reaction mixture was cooled on ice, and sodium sulfate decahydrate was added in order to decompose any excess hydride. Insoluble substances were removed by filtration, and the filtrate was concentrated by evaporation under reduced pressure. The concentrate was then purified by silica gel column chromatography, using a 7:3 by volume mixture of methylene chloride and methanol as the eluent, to give 151 mg (yield 59%) of the title compound as a colorless oily substance.

Workup

  1. temperaturecooling
  2. temperatureThe resulting mixture was then heated
  3. temperatureunder reflux for 1 hour
  4. additionwas added in order
  5. customInsoluble substances were removed by filtration
  6. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  7. customThe concentrate was then purified by silica gel column chromatography
  8. additionby volume mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-73cb71f68332420194032e3b6a893f77
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

Loading…