Imidazole → (R)-N-Boc-2-amino-1-(-tert-butyldimethylsilyloxy)-but-3-yne

Participants

Reaction Steps

To a solution of (R)-N-Boc-2-amino-but-3-yn-1-ol (150 mg, 0.81 mmol) (Example 104B) and imidazole (110 mg, 1.62 mmol) (Aldrich) in CH2Cl2 (10 mL) was added at 0° C. tert-butyldimethylsilyl chloride (146 mg, 0.97 mmol) (Fluka). After 5 min the reaction mixture was poured into H2O and extracted with CH2Cl2. The CH2Cl2 layer was dried over Na2SO4 and concentrated to a residue which after silica gel column chromatography with a 0-30% Et2O in hexanes gradient afforded the product. (Yield 210 mg, 83%).

Provenance & Evidence