Sodium borohydride → HCID 22290994, compound

HRID 967704Notes

Reaction equation

HRID 967704 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH3:18])=[N:10][N:11]2[CH2:14][C:15](=[O:17])[CH3:16])=[CH:7][CH:6]=1>CO>[CH3:3][O:4][C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH3:18])=[N:10][N:11]2[CH2:14][CH:15]([OH:17])[CH3:16])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22290993HCID 22290993, compound

Product 1

HCID 22290994HCID 22290994, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.21 g, 5.5 mmol) was added to a solution of the product from Step B (1.2 g, 5.5 mmol) in MeOH (10 ml) at room temperature. After stirring for 2 h at room temperature the solvent was evaporated and a saturated aqueous solution of ammonium chloride (10 mL) was added to the residue; this mixture was extracted with ethyl acetate (3×50 mL). The combined extracts were washed with brine (10 ml), dried (MgSO4) and evaporated to a residue which was purified by chromatography (silica, 20% to 30% ethyl acetate in hexane) to give an oil (0.68 g, 56%): MS (ES) m/z 221 (M+).

Workup

  1. customwas evaporated
  2. additiona saturated aqueous solution of ammonium chloride (10 mL) was added to the residue
  3. extractionthis mixture was extracted with ethyl acetate (3×50 mL)
  4. washThe combined extracts were washed with brine (10 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated to a residue which
  7. customwas purified by chromatography (silica, 20% to 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-43c4ba0f62d7489097ef6fff581f687d
Source dataset
uspto-grants-2005_10
Patent number
US06956036B1

Reaction notes

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