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

HRID 876801Notes

Reaction equation

HRID 876801 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-0e902d08eb0543d48737ba84b67a22d6
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

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