BOC-MET-OL

Into a 500 mL three-necked flask were added the starting compound as shown in the above route (49.8 g, 0.5mol) and 250 mL tetrahydrofuran. The temperature of the reaction mixture was adjusted to about 0-5°C in an ice-saltbath with agitation. To this mixture, sodium borohydride (19 g, 0.5 mol) was added slowly, followed by the addition of50 mL methanol. After addition, 100 mL solution of iodine (127 g, 0.5 mol) in tetrahydrofuran was added. Then, thereaction system was warmed to reflux. The reaction was continued for 2 h under agitation. After the raw material wasconsumed under the detecting of TLC, the temperature of the reaction mixture was adjusted with an ice-water bath.Saturated solution of ammonia chloride was added to quench the reaction. After 100 mL THF was evaporated out by arotary evaporator under reduced pressure, the residue was extracted with ethyl acetate (300 mL32).·The obtainedorganic layer was washed with dilute hydrochloric acid, followed by saturated sodium hydrogen carbonate, and finallyaqueous solution of sodium chloride. After drying and concentrating, a crude product (120 g) was obtained as an oil.The crude product was further treated by column chromatography to obtain a purified product (97.5 g). The yield was 85percent.1H NMR (400 MHz, CDCl3) δ 11.64(br, 1 H), 6.85 (br, 1 H), 4.55∼4.48 (m, 1 H), 2.53 (t, J = 4.9 Hz, 2H), 3.44 (s, 3H), 2.05 (s, 3H), 2.02∼1.87 (m, 2H), 1.48 (s, 9H). Ms (M++1): 236.Into a 500 mL three-necked flask were added the starting compound as shown in the above route (49.8 g, 0.5 mol) and 250 mL tetrahydrofuran. The temperature of the reaction mixture was adjusted to about 0-5° C. in an ice-salt bath with agitation. To this mixture, sodium borohydride (19 g, 0.5 mol) was added slowly, followed by the addition of 50 mL methanol. After addition, 100 mL solution of iodine (127 g, 0.5 mol) in tetrahydrofuran was added. Then, the reaction system was warmed to reflux. The reaction was continued for 2 h under agitation. After the raw material was consumed under the detecting of TLC, the temperature of the reaction mixture was adjusted with an ice-water bath. Saturated solution of ammonia chloride was added to quench the reaction. After 100 mL THF was evaporated out by a rotary evaporator under reduced pressure, the residue was extracted with ethyl acetate (300 mL×2). The obtained organic layer was washed with dilute hydrochloric acid, followed by saturated sodium hydrogen carbonate, and finally aqueous solution of sodium chloride. After drying and concentrating, a crude product (120 g) was obtained as an oil. The crude product was further treated by column chromatography to obtain a purified product (97.5 g). The yield was 85percent.

Molecular Weight:235.35
XLogP3:1.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:7
Exact Mass:235.12421471
Monoisotopic Mass:235.12421471
Topological Polar Surface Area:83.9
Heavy Atom Count:15
Complexity:192
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes