Sodium borohydride → HCID 66608179, compound

HRID 1529564Notes

Reaction equation

HRID 1529564 reaction equation
[BH4-].[Na+].C[O:4][C:5]([C:7]1[S:8][C:9]2[CH2:10][N:11]([C:16](=[O:24])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[F:23])[CH2:12][CH2:13][C:14]=2[N:15]=1)=O>CO.O>[F:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:16]([N:11]1[CH2:12][CH2:13][C:14]2[N:15]=[C:7]([CH2:5][OH:4])[S:8][C:9]=2[CH2:10]1)=[O:24]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 66609439HCID 66609439, compound

Product 1

HCID 66608179HCID 66608179, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium borohydride (0.035 g, 0.94 mmol) was added to a stirred suspension of 5-(2-fluorobenzoyl)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine-2-carboxylic acid methyl ester (0.25 g, 0.78 mmol) in MeOH (5 mL). The mixture was stirred at room temperature for 3 hours, diluted with H2O and extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The crude product was purified by preparative TLC (AcOEt in petroleum ether 50/50) to yield 5-(2-fluorobenzoyl)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine-2-methanol (0.18 g, 79% yield).

Workup

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customThe crude product was purified by preparative TLC (AcOEt in petroleum ether 50/50)

Sources & evidence

ORD record
ord-7e59977795e34e0e9617a56fbff12ae7
Source dataset
uspto-grants-2015_07
Patent number
US09090632B2

Reaction notes

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