Sodium borohydride → Thiazolo[4,5-c]pyridin-2-ylmethanol

HRID 1890555Notes

Reaction equation

HRID 1890555 reaction equation
[S:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]=[C:2]1[C:10](OCC)=[O:11].[BH4-].[Na+]>C(O)C>[S:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]=[C:2]1[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 65583458Ethyl thiazolo[4,5-c]pyridine-2-carboxylate

Product 1

HCID 55296405Thiazolo[4,5-c]pyridin-2-ylmethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl thiazolo[4,5-c]pyridine-2-carboxylate (R-3) (5 g, 24 mmol) in ethanol (100 mL) was added NaBH4 (0.9 g, 24 mmol) in portions at 0° C. The suspension was stirred at room temperature for 1 h, and then concentrated. The resulting residue was dissolved in EtOAc, washed with water. The organic layer was separated, dried over Na2SO4, concentrated in vacuo and purified by chromatography on silica gel to give the title compound. MS (m/z): 167 (M+1)+.

Workup

  1. concentrationconcentrated
  2. dissolutionThe resulting residue was dissolved in EtOAc
  3. washwashed with water
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-d897d3a298544ca19178d3db356dce84
Source dataset
uspto-grants-2013_08
Patent number
US08507487B2

Reaction notes

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