ETHYL (2-PHENYLETHYL)CARBAMATE

General Procedure for Compounds 2a-2h, 3a-3h, 4a-4h, 5a-5h, 6a-6h, 7a-7h, lla-h and 12a-12h. Ten mL of dichloromethane and a stir bar was added to 100-200 mg of the amine. Two equivalents of triethylamine was then added and the reaction mixture was cooled to 0 °C while stirring. Then, 0.9 equivalents of the chloroformate, isocyanate or thioisocyanate was added dropwise to the reaction mixture and was allowed to slowly warm to room temperature and continuted stirring overnight. The reaction mixture was then diluted with more dichloromethane, washed twice with IN HC1, washed twice with brine, dried with sodium sulfate and then concentrated in vacuo.; Ethyl N-(2-phenethyl) carbamate 2d was synthesized from commercially available materials by routine acylation methodology (ethyl chloroformate/TEA in DCM) (Scheme 1). Compound 2d was isolated in 96percent yield without recourse to chromatographic purification.Ethyl N-(2-phenethyl) carbamate 2d was synthesized from commercially available materials by routine acylation methodology (ethyl chloroformate/TEA in DCM) (Scheme 1). Compound 2d was isolated in 96percent yield without recourse to chromatographic purification.methyl 3-((R)-l-((R)-2-(3, 4-dimethoxyphenyl)-2-(l-oxo-l, 2, 3, 4- tetrahydroisoquinolin-7-ylamino)acetyl)pyrrolidin-2-yl)-4- (isopropylsulfonyl)phenylcarbamate; [00216] Ethyl chloroformate (20.8 g, 0.192 mol) was added dropwise to a solution of phenethylamine (15.5 g, 0.128mol) and triethylamine (180 mL) in diethyl ether (500 mL) while maintaining the internal temperature of the reaction below 10 Intermediate 1: 7-Amino-3, 4-dihydroisoquinolin-l(2H)-one; Intermediate IA:; [00188] Ethyl chloroformate (20.8 g, 0.192 mol) was added dropwise to a solution of phenethylamine (15.5 g, 0.128 mol) and triethylamine (180 mL) in diethyl ether (500 mL) while maintaining the internal temperature of the reaction below 10 Step 1: 4.2.4.9. Ethyl phenethylcarbamate (42). Converted to the N-phenylacetamide derivative using the general procedure describedand with the following alterations: phenethylamine (0.31 mL, 2.5 mmol) dissolved in CH2Cl2 (10 mL) followed by the additionof TEA (0.69 mL, 5.0 mmol) which was cooled to 0 °C. Ethyl chloro-formate (0.21 mL, 2.20 mmol) added dropwise at 0 °C, stirred for24 h at rt, and concentrated. Resulting material dissolved in CH2Cl2and washed sequentially with 15 mL of the following solutions:1 M HCl, H2O, sat. NaHCO3, H2O, and brine. Organic layer concen-trated and dissolved in EtOAc. The solution was heated followedby the addition of cold hexane to result in precipitation. Solutioncooled to 0 °C and precipitate collected through ltration. Productwas obtained as a white powder (yield: 0.12 g, 29percent). Mp 35–36 °C.1H NMR (500 MHz, CDCl3) d 7.20–7.36 (m, 5H), 4.71 (br s, 1H), 4.14(q, J = 7.0 Hz, 2H), 3.46 (t, 2H), 2.84 (t, J = 6.9 Hz, 2H), 1.26 (t, 3H).13C NMR (125 MHz, CDCl3) d 156.8, 139.0, 128.9, 128.7, 126.7, 60.9, 42.3, 36.4, 14.8. DART-HRMS (m/z) calculated for C11H16NO2[M+H]+ 194.1181, found 194.1209.To a solution of phenethylamine (60.5 g, 0.5 mol) and Na

Molecular Weight:193.24
XLogP3:2.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:5
Exact Mass:193.110278721
Monoisotopic Mass:193.110278721
Topological Polar Surface Area:38.3
Heavy Atom Count:14
Complexity:165
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes