Sodium Chloride → HCID 54267952, compound

HRID 486718Notes

Reaction equation

HRID 486718 reaction equation
[Br-].[Li+].[BH4-].[Na+].[C:5]([O:9][C:10]([C@@H:12]1[CH2:16][S:15][C@@H:14]([C:17](OCC)=[O:18])[CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].[Cl-].[NH4+].[Cl-].[Na+]>C(O)C>[C:5]([O:9][C:10]([C@@H:12]1[CH2:16][S:15][C@@H:14]([CH2:17][OH:18])[CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 25517Ammonium ChlorideHCID 82050Lithium BromideHCID 4311764Sodium borohydrideHCID 53995661HCID 53995661, compound

Product 1

HCID 54267952HCID 54267952, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Lithium bromide (686 mg) and sodium borohydride (165 mg) were dissolved in ethanol (6 ml) and under nitrogen atmosphere the mixture was stirred for 1 hour at room temperature. To the mixture, trans-4-tert-butoxycarbonyl-2-ethoxycarbonyltetrahydrothiophene (ref. compound No. 1, 567 mg) dissolved in ethanol (2 ml) was added at room temperature and the mixture was stirred for 18 hours. Aqueous ammonium chloride solution and saturated sodium chloride solution were added to the mixture and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 436 mg (99%) of the titled compound (compound No. 1-1).

Workup

  1. additionwas added at room temperature
  2. stirringthe mixture was stirred for 18 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe oily residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-0de379dfa83e42878f8925058de75224
Source dataset
uspto-grants-1994_03
Patent number
US05292767

Reaction notes

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