Hydrochloric Acid → HCID 86657900, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2-hydroxy-ethyl)-methyl-carbamic acid tert-butyl ester (CAS Nr. 57561-39-4; 2.50 g, 14.3 mmol) in toluene (35 ml) was added powered KOH (2.8 g, 50 mmol) and Bu4NHSO4 (0.97 mg, 2.86 mmol). The reaction mixture was stirred vigorously and heated to 50° C. while neat 1-bromo-2-fluoro-ethane (2.72 g, 21.4 mmol) was added slowly. The temperature was increased to 80° C. and maintained for 3-5 h. The reaction mixture was cooled to RT, water was added (50 ml) and the pH was adjusted to 7 with 1N HCl solution. Extraction with EtOAc (2×150 ml), washing with brine, drying with Na2SO4 and concentrating under vacuum yielded the crude product. The crude material was subjected to column chromatography on silica by EtOAc:hexane (10:90 to 20:80) to give the desired product as light yellow liquid (1.2 g, 38%). MS (m/z)=122.0 [M−Boc+]; 166.2 [M−tBu+].

Provenance & Evidence