تفاعل #1165337

معادلة التفاعل

2'-[(t-butoxycarbonylamino)methyl]-4-[(t-butyldiphenylsiloxy)methyl]-1,1'-biphenyl

tetra-n-butylammonium fluoride

→

product

المردود 92.1%

2'-[(t-Butoxycarbonylamino)methyl]-1,1'-biphenyl-4-methanol

المردود 92.1%

المذيبات

tetrahydrofuran

tetrahydrofuran

diethyl ether

ظروف التفاعل

المعالجة

1. 1
   غسيلThe mixture was washed with water (3×150 mL), saturated aqueous sodium bicarbonate (50 mL), saturated aqueous sodium chloride (50 mL)
2. 2
   تجفيفdried over magnesium sulfate
3. 3
   ترشيحfiltered
4. 4
   أخرىThe solvent was removed under vacuum
5. 5
   أخرىto give an oil which
6. 6
   أخرىwas purified by column chromatography on silica gel eluting with hexanes/ethyl acetate (55:45)

الإجراء التجريبي

To a solution of 3.85 g (7.00 mmol) of 2'-[(t-butoxycarbonylamino)methyl]-4-[(t-butyldiphenylsiloxy)methyl]-1,1'-biphenyl (Step D) in 25 mL of dry tetrahydrofuran under a nitrogen atmosphere was added by syringe 10.5 mL (0.530 mmol) of a 1.0M solution of tetra-n-butylammonium fluoride in tetrahydrofuran. The reaction mixture was stirred for two hours then diluted with 700 mL of diethyl ether. The mixture was washed with water (3×150 mL), saturated aqueous sodium bicarbonate (50 mL), saturated aqueous sodium chloride (50 mL), then dried over magnesium sulfate and filtered. The solvent was removed under vacuum to give an oil which was purified by column chromatography on silica gel eluting with hexanes/ethyl acetate (55:45) to afford 2.02 g (92%) of the product as a white solid (mp 89°-93° C.). 1H NMR (200 MHz, CDCl3): δ1.40 (s, 9H), 2.50 (s, 2H), 4.20 (s, 2H), 4.70 (s, 2H), 7.18-7.45 (m, 8H). FAB-MS: calculated for C19H23NO3 313; found 314 (M+H).

المصدر