Sodium borohydride → HCID 86695276, compound

HRID 709413Notes

Reaction equation

HRID 709413 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8]([NH:10][C:11]1[S:15][C:14]([C:16](OCC)=[O:17])=[N:13][CH:12]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>CO>[OH:17][CH2:16][C:14]1[S:15][C:11]([NH:10][C:8](=[O:9])[O:7][C:3]([CH3:5])([CH3:4])[CH3:6])=[CH:12][N:13]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 46942156Ethyl 5-[(tert-butoxycarbonyl)amino]-1,3-thiazole-2-carboxylate2×

Product 1

HCID 86695276HCID 86695276, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (1.1 g, 29.2 mmol) was added portion wise to a solution of Ethyl 5-(tert-butoxycarbonyl amino)thiazole-2-carboxylate (Intermediate Z, 4 g, 14.6 mmol) in MeOH (40 mL) at 0° C. over a period of 30 mins and stirred at RT for 16 h. After completion, solvent was evaporated, the solid residue was dissolved in ice water (50 mL) and extracted with EtOAc (2×50 mL) The combined extracts were washed with water (50 mL), brine (50 mL), dried over anhydrous Na2SO4, filtered and evaporated. The crude was purified by column chromatography by using SiO2, eluting with EtOAc:Petroleum ether (2:8) to afford Tert-butyl (2-(hydroxymethyl)thiazol-5-yl)carbamate (2.9 g, 84.8%) as white solid.

Workup

  1. customAfter completion, solvent was evaporated
  2. dissolutionthe solid residue was dissolved in ice water (50 mL)
  3. extractionextracted with EtOAc (2×50 mL) The combined extracts
  4. washwere washed with water (50 mL), brine (50 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude was purified by column chromatography
  9. washeluting with EtOAc:Petroleum ether (2:8)

Sources & evidence

ORD record
ord-13d43246093849ddae8551cb140e6011
Source dataset
uspto-grants-2015_11
Patent number
US09181198B2

Reaction notes

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