Hydrochloric Acid → 4-Hydroxytetrahydropyran-3-sulfonamide

HRID 72344Notes

Reaction equation

HRID 72344 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][O:5][CH2:4][CH:3]1[S:8]([NH2:11])(=[O:10])=[O:9].[BH4-].[Na+].Cl>C1COCC1.CO>[OH:1][CH:2]1[CH2:7][CH2:6][O:5][CH2:4][CH:3]1[S:8]([NH2:11])(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 682926194-Oxotetrahydropyran-3-sulfonamide

Product 1

HCID 682929934-Hydroxytetrahydropyran-3-sulfonamideYield 59%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

4-Oxotetrahydropyran-3-sulfonamide (1.09 g) was dissolved in 2:1 THF/methanol (110 ml), sodium borohydride (0.23 g) was added in portions and the mixture was stirred at room temperature for 18 hours. Concentrated hydrochloric acid was then used to set the pH to 2 and then the solvent was removed under reduced pressure. The residue was purified by chromatography (solvent: dichloromethane/methanol). This gave the product (0.65 g) with a molecular weight of 181.2 g/mol (C5H11NO4S).

Workup

  1. additionwas added in portions
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified by chromatography (solvent: dichloromethane/methanol)

Sources & evidence

ORD record
ord-d3bdbb88e81a4615b55d6d78c89d59e3
Source dataset
uspto-grants-2014_09
Patent number
US08828995B2

Reaction notes

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