Hydrochloric Acid → HCID 58307570, compound

HRID 1516452Notes

Reaction equation

HRID 1516452 reaction equation
[F:1][C:2]1[C:3]([OH:16])=[C:4]([CH2:11][CH:12]([OH:15])CO)[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[BH4-].[Na+].Cl>O.CC(C)=O>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([CH2:11][CH2:12][OH:15])[C:3]=1[OH:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 58307569HCID 58307569, compound

Product 1

HCID 58307570HCID 58307570, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 180AcetoneCatalystHCID 962WaterSolvent

Procedure

Compound 4 (3.7 g, 16 mmol) was suspended in water and dissolved by adding a few drops of acetone. NaIO4 (3.42 g, 16 mmol) was added portionwise at 0° C. After 7 min NaBH4 (4.84 g, 128 mmol) was added slowly. The solution was stirred for 1 h at room temperature, the acidified with dilute hydrochloric acid and extracted with ethyl acetate. The filtrate was concentrated to yield the desired compound 5 (2.4 g, yield 75%).

Workup

  1. dissolutiondissolved
  2. extractionextracted with ethyl acetate
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ba01258b0e244799861b5b745456cf3a
Source dataset
uspto-grants-2012_07
Patent number
US08227501B2

Reaction notes

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