BENZYL 2-BROMOETHYLCARBAMATE

A cooled (0° C.) mixture of 2-bromoethylamine hydrobromide (12.000 g ; 58.56 mmol ; 1.0 eq.) in dioxane (60 ml) was treated with aq. 1M NaOH (117.2 ml ; 117.20 mmol ; 2.0 eq.), and dropwise (over 10 min.) with benzyl chloroformate (8.4 ml ; 58.8 mmol ; 1.0 eq.). The resulting mixture was further stirred at 0° C., under nitrogen, for 10 min., and then at rt for 13 h. EtB.3 /V-alkylation of imidazoles with Br(CHTreat a 0 °C solution of 2-bromoethylamine hydrobromide (50 g, 0.246 mol) in dioxane (500 mL) with aqueous NaOH (1 M, 492 mL, 0.492 mol), add benzyl chloroformate (21.6 g, 0.127 mol) drop-wise, warm to RT and stir overnight. Pour the mixture into HGeneral Synthesis Instructions for N-Z-2-bromoethylamine/N-Z-3-bromopropylamine: Add a solution of 1.5 equivalents of benzylchloroformiate in 50 ml Rotisol in drops to a solution of one equivalent of 2-bromoethylamine-hydrobromide or 3-bromopropylamine-hydrobromide and three equivalents of triethylamine in 150 ml Rotisol under refrigeration. Stir for 20 hours at room temperature, then concentrate the formulation to a small volume, take it up in 200 ml ethyl acetate, and extract twice against 200 ml 2 N hydrochloric acid each time. Remove the solvent and purify the residue via column chromatography on 100 g silica gel. Elute the apolar impurities with cyclohexane/diisopropyl ether (10:1), and elute the product with diisopropyl ether; N-Z-2-bromoethylamine (72): Quantities Used: 34.8 g (170 mmol) 2-bromoethylamine-hydrobromide, 72.0 ml (255 mmol) 50percent solution of benzylchloroformiate in toluene, 70.6 ml (510 mmol) triethylamineTo a solution of 2-bromoethylamine bromide (5 g, 24.4 mmole) in DMF (50 mL) was added diisopropylethylamine (8.5 mL, 48.8 mmole) and benzyl chloroformate (3.48 mL, 24.4 mmole). The mixture thus obtained was stirred at room temperature for 2 hours. The reaction mixture was concentrated and the residue was purified by flash chromatography on silica gel with ethyl acetate/hexanes (3/7) as eluent to give the desired compound 34 as an oil (4 g, 64percent). Synthesis of Compound 1: To a solution of 2-bromoethylamine bromide (5 g, 24.4 mmole) in DMF (50 mL) was added diisopropylethylamine (8.5 mL, 48.8 mmole) and benzyl chlroroformate (3.48 mL, 24.4 mmole). The mixture thus obtained was stirred at room temperature for 2 hours. The reaction mixture was concentrated and the residue was purified by flash chromatography on silica gel with ethyl acetate/hexanes (3/7) as gradient to give Compound 1 as an oil (4 g, 64percent).

Molecular Weight:258.11
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:5
Exact Mass:257.00514
Monoisotopic Mass:257.00514
Topological Polar Surface Area:38.3
Heavy Atom Count:14
Complexity:170
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes