反応 #155403

反応方程式

N-Boc-3-methylene-cyclobutanamine

K2CO3

→

N-Boc-3-amino-cyclobutanone

収率 177.6%

溶媒

DCM

H2O

反応条件

後処理

1. 1
   その他During the course of the reaction
2. 2
   ろ過upon completion, the reaction mixture was filtered through a pad of celite
3. 3
   その他The filtrates were transferred to a separatory funnel
4. 4
   抽出the aqueous layer was extracted with DCM (2×50 mL)
5. 5
   洗浄The combined organic layers were washed with 5% NaHCO3 (2×30 mL), brine (30 mL)
6. 6
   乾燥dried over Na2SO4
7. 7
   ろ過filtered
8. 8
   その他evaporated to dryness
9. 9
   その他to yield a crude, which
10. 10
    その他was purified by flash chromatography (silica gel/hexanes:ethyl acetate 0-60%)

実験手順

To a vigorously stirring solution of N-Boc-3-methylene-cyclobutanamine (9.8 g, 53.5 mmol) in DCM (160 mL) and H2O (160 mL) was added K2CO3 (3 g, 21.7 mmol), followed by NaClO4 (35 g, 163.5 mmol), tetrabutylammonium chloride (0.2 g, 0.72 mmol) and RuCl3 (0.6 g, 7.6 mmol). During the course of the reaction, the organic solution turned dark brown, the catalyst turned black, while the upper aqueous layer turned white. The reaction was monitored by TLC, and upon completion, the reaction mixture was filtered through a pad of celite. The filtrates were transferred to a separatory funnel, and the aqueous layer was extracted with DCM (2×50 mL). The combined organic layers were washed with 5% NaHCO3 (2×30 mL), brine (30 mL), dried over Na2SO4, filtered and evaporated to dryness to yield a crude, which was purified by flash chromatography (silica gel/hexanes:ethyl acetate 0-60%) to yield the desired N-Boc-3-amino-cyclobutanone (7.13 g, 38.53 mmol, 72% yield): NMR (250 MHz, CDCl3) δ 4.88 (bs, 1H), 4.13-4.29 (m, 1H), 3.23-3.41 (m, 2H), 2.9-3.05 (m, 2H), 1.39 (s, 9H).

出典