Hydrochloric Acid → HCID 69939986, compound

Reaction equation

C(S([NH:7][CH:8]([C:10]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:11]=1[CH2:12][OH:13])[CH3:9])=O)(C)(C)C.Cl.O1CCOCC1>CO>[NH2:7][CH:8]([C:10]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:11]=1[CH2:12][OH:13])[CH3:9]

Participants

Procedure

To a stirred solution of 2-(1-tert-butylsulfinamidylethyl)-5-chlorobenzyl alcohol from step 2 of the L-519,502 synthesis (isomer 2, 0.654 g, 2.23 mmol) in MeOH (10 mL) at ambient temperature was added 4M HCl in dioxane (1.12 mL, 4.46 mmol). The resulting solution was stirred at ambient temperature for 0.5 h, then concentrated in vacuo. The residue was partitioned between EtOAc and water basified to pH=8 with saturated NaHCO3 solution. The EtOAc layer was separated, dried over anhydrous Na2SO4, and filtered. The filtrate solvent was removed under reduced pressure. 2-(1-aminoethyl)-5-chlorobenzyl alcohol was obtained as a pink oil that crystallizes on sitting (0.3 g; HPLC RT=2.07 min, method A; 1H NMR, 400 MHz, CDCl3, 7.32 ppm (d, 1H), 7.29 ppm (d, 1H), 7.24 ppm (dd, 1H), 4.76 ppm (d, 1H), 4.65 ppm (d, 1H), 4.34 ppm (q, 1H), 3.4 ppm (br s, 3H), 1.7 ppm (d, 3H).