Sodium borohydride → HCID 18516204, compound

HRID 1369629Notes

Reaction equation

HRID 1369629 reaction equation
[BH4-].[Na+].[Cl-].[Cl-].[Ca+2].C([O:8][C:9]([C:11]1[CH:16]=[N:15][CH:14]=[C:13]2[S:17][C:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:19][C:12]=12)=O)C>CO.C1COCC1>[OH:8][CH2:9][C:11]1[CH:16]=[N:15][CH:14]=[C:13]2[S:17][C:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:19][C:12]=12

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 18516224HCID 18516224, compound

Product 1

HCID 18516204HCID 18516204, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent2×

Procedure

To a stirred solution of NaBH4 (0.18 g, 4.89 mmol) in anhydrous 50% MeOH/THF at 0° C. was added powdered CaCl2 (0.54 g, 4.89 mmol). The suspension was stirred 20 minutes and a solution of Example 237D (0.50 g, 1.63 mmol) in anhydrous 50% MeOH/THF was slowly added over a period of 10 minutes. The reaction stirred 1 hour at 0° C. followed by 16 hours at room temperature. Reaction was quenched into a slurry of dilute AcOH (aq)/ice. After all gas evolution ceased with occasional stirring, aqueous was made basic with sat. NaHCO3. Aqueous was extracted with dichloromethane (3×40 mL) and extracts combined. The organic phase was dried (Na2SO4), filtered, and concentrated. The residue was purified by flash chromatography on silica gel using EtOAc/hexane as eluent to provide dimethylethyl 4-(hydroxymethyl)-thieno[2,3-c]pyridine-2-carboxylate compound as a solid (0.14 g, 32%).

Workup

  1. stirringThe reaction stirred 1 hour at 0° C.
  2. waitfollowed by 16 hours at room temperature
  3. customReaction
  4. customwas quenched into a slurry of dilute AcOH (aq)/ice
  5. extractionAqueous was extracted with dichloromethane (3×40 mL)
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-54ce318064c644e99c432fc46adfa68e
Source dataset
uspto-grants-2003_06
Patent number
US06579882B2

Reaction notes

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