Sodium borohydride → Ethyl-3-[2-[(4-chlorophenyl)sulfonylaminomethyl]indan-5-yl]propionate

HRID 1654961Notes

Reaction equation

HRID 1654961 reaction equation
[CH2:1]([O:3][C:4](=[O:28])/[CH:5]=[CH:6]/[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH:11]([CH2:16][NH:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH2:10]2)[CH3:2].[BH4-].[Na+]>C(O)C>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH:11]([CH2:16][NH:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH2:10]2)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18921490HCID 18921490, compound

Product 1

HCID 18921500Ethyl-3-[2-[(4-chlorophenyl)sulfonylaminomethyl]indan-5-yl]propionateYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

387 mg (1.00 mmol) of ethyl-trans-3-[2-[(4chlorophenyl)sulfonylaminomethyl]indan-5-yl]acrylate was dissolved in 10 ml of ethanol, to which was added 24 mg (0.1 mmol)of nickel chloride·6H2O. Under ice-cooling, to this solution was added 76 mg (2.00 mmol) of sodium borohydride, followed by stirring at room temperature overnight. The ethanol was distilled off, the residue was added with 10 ml of water, and the obtained product was extracted with ethyl acetate, followed by washing and drying then condensing. The obtained crystals were recrystallized from a solvent mixture of hexane and ether to obtain 241 mg colorless crystals. Yield: 62%

Workup

  1. temperatureUnder ice-cooling, to this solution
  2. distillationThe ethanol was distilled off
  3. additionthe residue was added with 10 ml of water
  4. extractionthe obtained product was extracted with ethyl acetate
  5. washby washing
  6. customdrying
  7. customcondensing
  8. customThe obtained crystals were recrystallized from a solvent mixture of hexane and ether

Sources & evidence

ORD record
ord-b0ea29514ae1462c8beb4c67fe0eb709
Source dataset
uspto-grants-1995_04
Patent number
US05409956

Reaction notes

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