تفاعل #409220

معادلة التفاعل

N-(t-butoxycarbonyl)-2-bromobenzylamine

4-(t-butyldiphenylsilyoxymethyl)phenylboronic acid

sodium hydroxide

isopropanol

→

product

المردود 100.0%

2′-[(t-Butoxycarbonylamino)methyl]4-[(t-butyldiphenylsiloxy)methyl]-1,1′-biphenyl

المردود 100.0%

المذيبات

water

benzene

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe resulting mixture was heated under nitrogen
2. 2
   درجة الحرارةat reflux for 2 hours
3. 3
   أخرىtransferred to a separators funnel
4. 4
   استخلاصextracted with ether (3×150 mL)
5. 5
   غسيلThe combined ether extracts were washed with saturated aqueous sodium bicarbonate (100 mL) and saturated aqueous sodium chloride (100 mL)
6. 6
   تجفيفdried over magnesium sulfate
7. 7
   ترشيحfiltered
8. 8
   أخرىThe solvent was removed under vacuum
9. 9
   أخرىto give a crude product which
10. 10
    أخرىwas purified by column chromatography on silica gel eluting with hexaneslethyl acetate (9:1)

الإجراء التجريبي

To a solution of 3.2 g (8.2 mmol) of 4-(t-butyldiphenylsilyoxymethyl)phenylboronic acid (Step C) in 64 mL of benzene was added 2.2 mL of water, 6.4 mL of 5N aqueous sodium hydroxide, and 8.3 mL of isopropanol. To this mixture was added 180 mg (0.16 mmol) of tetrakis(triphenylphosphine) palladium and 2.20 g (7.81 mmol) of N-(t-butoxycarbonyl)-2-bromobenzylamine (Step D). The resulting mixture was heated under nitrogen at reflux for 2 hours then cooled to room temperature. The reaction mixture was diluted with 100 mL of water, transferred to a separators funnel and extracted with ether (3×150 mL). The combined ether extracts were washed with saturated aqueous sodium bicarbonate (100 mL) and saturated aqueous sodium chloride (100 mL), dried over magnesium sulfate and filtered. The solvent was removed under vacuum to give a crude product which was purified by column chromatography on silica gel eluting with hexaneslethyl acetate (9:1) to afford 4.31 g (100%) of the product as a clear oil. 1H NMR (200 MHz, CDCl3): d 1.11 (s, 9 H), 1.41 (s, 9 H), 4.27 (d, 6 Hz, 2 H), 4.45 (m, 1 H), 4.81 (s, 2 H), 7.20-7.49 (m, 14 H), 8.72 (m, 4 H). FAB-MS: calculated for C35H41NO3Si 551; found 552 (M+H).

المصدر