반응 #155403

반응 방정식

N-Boc-3-methylene-cyclobutanamine

K2CO3

→

N-Boc-3-amino-cyclobutanone

수율 177.6%

용매

DCM

H2O

반응 조건

후처리

1. 1
   기타During the course of the reaction
2. 2
   여과upon completion, the reaction mixture was filtered through a pad of celite
3. 3
   기타The filtrates were transferred to a separatory funnel
4. 4
   추출the aqueous layer was extracted with DCM (2×50 mL)
5. 5
   세척The combined organic layers were washed with 5% NaHCO3 (2×30 mL), brine (30 mL)
6. 6
   건조dried over Na2SO4
7. 7
   여과filtered
8. 8
   기타evaporated to dryness
9. 9
   기타to yield a crude, which
10. 10
    기타was purified by flash chromatography (silica gel/hexanes:ethyl acetate 0-60%)

실험 절차

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).

출처