Hydrochloric Acid → HCID 68268574, compound

HRID 874754Notes

Reaction equation

HRID 874754 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[CH:11]1[S:16][CH2:15][CH:14]([OH:17])[CH:13]=[C:12]1[N+:18]([O-:20])=[O:19].Cl.C([O-])(O)=O.[Na+]>CO.CCOC(C)=O>[F:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[C@H:11]1[S:16][CH2:15][CH:14]([OH:17])[CH2:13][C@@H:12]1[N+:18]([O-:20])=[O:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 68268704HCID 68268704, compound

Product 1

HCID 68268574HCID 68268574, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium borohydride (190 mg, 5.03 mmol) 37.8 was added over 10 min to an ice cold solution of 6-(2,5-difluorophenyl)-5-nitro-3,6-dihydro-2H-thiopyran-3-ol (570 mg, 2.08 mmol) in MeOH (25 mL). The mixture was slowly warmed to room temperature and stirred for an additional 18 h. The orange solution was cooled in an ice bath and 2N HCl (2.6 mL, 5.2 mmol) was added dropwise. After 5 min, the solution was added to a mixture of EtOAc (100 mL) and saturated aqueous NaHCO3 (50 mL), the aqueous layer was re-extracted with additional EtOAc (2×50 mL), the combined EtOAc layers were washed with brine (1×50 mL), dried with MgSO4, filtered and evaporated to give the title compound as a foam.

Workup

  1. temperatureThe orange solution was cooled in an ice bath
  2. waitAfter 5 min
  3. extractionthe aqueous layer was re-extracted with additional EtOAc (2×50 mL)
  4. washthe combined EtOAc layers were washed with brine (1×50 mL)
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-41cde0ad1b12453ea07b3d4a5ab819c1
Source dataset
uspto-grants-2015_03
Patent number
US08980929B2

Reaction notes

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