反応 #170903

反応方程式

(R)-[1-(4-bromo-benzenesulfonyl)-pyrrolidin-2-yl]-methanol

3-amino-phenyl boronic acid

potassium carbonate

water

→

(R)-(1-(3′-aminobiphenyl-4-ylsulfonyl)pyrrolidin-2-yl)methanol

収率 49.0%

溶媒

DMF

反応条件

後処理

1. 1
   その他The resulting mixture was degassed by gently bubbling argon through the solution for 5 minutes at 20° C
2. 2
   ろ過The reaction was filtered through a pad of silica gel, which
3. 3
   洗浄was washed with CH2Cl2 (25 mL×3)
4. 4
   濃縮The combined organics were concentrated under reduced pressure
5. 5
   その他to give the crude product, which
6. 6
   洗浄was washed with EtOAc

実験手順

To a solution of (R)-[1-(4-bromo-benzenesulfonyl)-pyrrolidin-2-yl]-methanol (1.6 g, 5.0 mmol) in DMF (10 mL) was added 3-amino-phenyl boronic acid (0.75 g, 5.5 mmol), Pd(PPh3)4 (45 mg, 0.15 mmol), potassium carbonate (0.75 g, 5.5 mmol) and water (5 mL). The resulting mixture was degassed by gently bubbling argon through the solution for 5 minutes at 20° C. The reaction mixture was then heated at 80° C. overnight. The reaction was filtered through a pad of silica gel, which was washed with CH2Cl2 (25 mL×3). The combined organics were concentrated under reduced pressure to give the crude product, which was washed with EtOAc to give pure (R)-(1-(3′-aminobiphenyl-4-ylsulfonyl)pyrrolidin-2-yl)methanol (C-2) (810 mg, 49%). 1H NMR (300 MHz, CDCl3) δ 7.88 (d, J=8.7 Hz, 2H), 7.70 (d, J=8.7 Hz, 2H), 7.23-7.28 (m, 1H), 6.98 (d, J=7.8 Hz, 1H), 6.91 (d, J=1.8 Hz, 1H), 6.74 (dd, J=7.8, 1.2 Hz, 1H), 3.66-3.77 (m, 3H), 3.45-3.53 (m, 1H), 3.26-3.34 (m, 1H), 1.68-1.88 (m, 3H), 1.45-1.55 (m, 1H). MS (ESI) m/e (M+H+) 333.0.

出典