Sodium borohydride → HCID 18364412, compound

HRID 380245Notes

Reaction equation

HRID 380245 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:24]=[CH:23][C:7]([O:8][C:9]2[C:10]3[CH:19]=[C:18]4[O:20][CH2:21][O:22][C:17]4=[CH:16][C:11]=3[S:12][C:13]=2[CH:14]=[O:15])=[CH:6][CH:5]=1>CO>[CH2:21]1[O:22][C:17]2[C:18](=[CH:19][C:10]3[C:9]([O:8][C:7]4[CH:23]=[CH:24][C:4]([Cl:3])=[CH:5][CH:6]=4)=[C:13]([CH2:14][OH:15])[S:12][C:11]=3[CH:16]=2)[O:20]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 15482077HCID 15482077, compound

Product 1

HCID 18364412HCID 18364412, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

26 mmol of NaBH4 are added at ambient temperature to a solution of 24 mmol of the compound obtained in Step E of Example 1 in 100 ml of methanol. After reacting for 2 hours, one equivalent of NaBH4 is added to the reaction mixture. After reacting for 12 hours, the solution is concentrated and then diluted with ethyl acetate, washed with 1N HCl solution, then with water and then with saturated NaCl solution, subsequently dried over calcium sulphate, filtered and concentrated under reduced pressure. Chromatography over silica gel (dichloromethane/ethyl acetate: 95/5) allows the expected product to be isolated.

Workup

  1. waitAfter reacting for 12 hours
  2. concentrationthe solution is concentrated
  3. additiondiluted with ethyl acetate
  4. washwashed with 1N HCl solution
  5. dry with materialwith water and then with saturated NaCl solution, subsequently dried over calcium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto be isolated

Sources & evidence

ORD record
ord-a8be851ff36148bfa3ddd7ebfa37f73d
Source dataset
uspto-grants-2001_10
Patent number
US06302837B1

Reaction notes

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