Nitrogen → 5-(((Tert-butyldimethylsilyl)oxy)methyl)thiazole-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-bromo-5-(((tert-butyldimethylsilyl)oxy)methyl)thiazole (WO 2009/077990, p. 92) (2.0 g, 6.49 mmol) in Et2O (14.0 mL) was treated dropwise at −70° C. with n-BuLi (4.25 mL of a 1.6M solution in hexane, 6.81 mmol). The resulting mixture was stirred for 30 min at −70° C. DMF (0.80 mL, 10.38 mmol) was then added and the resulting mixture was stirred for 20 min at −70° C. Sat. aq. NH4Cl was added, the org. layer was extracted with EA (3×20 mL) and the combined org. layers were dried over MgSO4, filtered and the solvent was removed under reduced pressure to give 1.50 g of 5-(((tert-butyldimethylsilyl)oxy)methyl)thiazole-2-carbaldehyde as a yellow oil: TLC: rf (9:1 hept-EA)=0.31. LC-MS-conditions 07: tR=1.00 min, [M+H]+=257.93. A solution of this material in MeOH (10 mL) was treated at 0° C. with NaBH4 (286 mg, 7.25 mmol). After 30 min at 0° C., water followed by EA were added. The org. layer was extracted with EA (3×20 mL) and the combined org. layers were dried over Na2SO4, filtered and the solvent was removed under reduced pressure. Purification of the residue by FC (1:1 hept-EA) gave the title compound as a yellow oil: TLC: rf (1:1 hept-EA)=0.33. LC-MS-conditions 07: tR=0.87 min, [M+H]+=260.06.

Provenance & Evidence