Sodium borohydride → HCID 58284857, compound

HRID 2368834Notes

Reaction equation

HRID 2368834 reaction equation
[N:1]1([C:10]2[S:14][C:13]([C:15](=[O:20])[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:12][CH:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[BH4-].[Na+]>CO>[N:1]1([C:10]2[S:14][C:13]([CH:15]([OH:20])[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:12][CH:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58284825HCID 58284825, compound

Product 1

HCID 58284857HCID 58284857, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
2.5 °C

Procedure

The compound (84) (0.703 mmoles) was dissolved in methanol (10 ml), cooled to 0-5° C., added sodium borohydride in lots at 0-5° C. in 5 minutes, after completion of addition, the reaction mixture was warmed to 25 to 30° C., stirred for 2.0 hrs. After completion of reaction, quenched the reaction with water (10 ml) and extracted in ethyl acetate (2×100 ml), washed with 10% brine, and dried over sodium sulphate. Distilled off the ethyl acetate completely to residue to get the crude compound, The crude compound was purified by using silica gel 60-120 silica gel column chromatography and DCM: methanol: 100-5% as mobile phase to get the pure compound (85).

Workup

  1. additionafter completion of addition
  2. temperaturethe reaction mixture was warmed to 25 to 30° C.
  3. customAfter completion of reaction
  4. customquenched
  5. customthe reaction with water (10 ml)
  6. extractionextracted in ethyl acetate (2×100 ml)
  7. washwashed with 10% brine
  8. dry with materialdried over sodium sulphate
  9. distillationDistilled off the ethyl acetate completely to residue
  10. customto get the crude compound
  11. customThe crude compound was purified

Sources & evidence

ORD record
ord-c0f308dfb60941d098fd7fb76bc7edbb
Source dataset
uspto-grants-2014_04
Patent number
US08703811B2

Reaction notes

Loading…