Sodium borohydride → Methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-propyl]-octanoate

HRID 465524Notes

Reaction equation

HRID 465524 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.O.O.O.O.O.O.[Co](Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydride2×HCID 53687026Methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-oct-2-enoate

Product 1

HCID 10479691Methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-propyl]-octanoate

Reagents, catalysts & solvents 2

HCID 517166Dichlorocobalt hexahydrateCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3.27 g (7 mmol) of methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-oct-2-enoate (example 3) in 32 ml methanol, 0.446 g (1.87 mmol) cobalt (II) chloride hexahydrate is added. The solution is cooled in an ice bath and 0.573 g (15 mmol) sodium borohydride is added in small portions. Vigorous gas evolution and formation of a black precipitate is observed during the addition of sodium borohydride. After completion of the addition, the ice bath is removed and the mixture stirred at room temperature for 1 h. The black precipitate is filtered off and washed with methanol. The combined filtrate is evaporated and the residue suspended in a mixture of 30 ml methylene chloride and 150 ml ether. The organic layer is washed with water. The aqueous phase is extracted with ether (2×50 ml). The combined organic extract is dried (MgSO4), filtered and the solvent evaporated. The residue is subjected to flash chromatography on silica using 3:2 ethyl acetate/hexane as the eluent to give methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-octanoate, m.p. 81°-82°.

Workup

  1. temperatureThe solution is cooled in an ice bath
  2. additionAfter completion of the addition
  3. customthe ice bath is removed
  4. filtrationThe black precipitate is filtered off
  5. washwashed with methanol
  6. customThe combined filtrate is evaporated
  7. additionthe residue suspended in a mixture of 30 ml methylene chloride and 150 ml ether
  8. washThe organic layer is washed with water
  9. extractionThe aqueous phase is extracted with ether (2×50 ml)
  10. extractionThe combined organic extract
  11. dry with materialis dried (MgSO4)
  12. filtrationfiltered
  13. customthe solvent evaporated

Sources & evidence

ORD record
ord-45e35facaa5e46c3b98b13e334ee8384
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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