Sodium cyanoborohydride → N-(7-chloro-1,2,3,4-tetrahydro-naphthalen-1-yl)-O-methyl-hydroxylamine
반응식
[CH3:1][O:2][N:3]=[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:14])[CH:12]=2)[CH2:7][CH2:6][CH2:5]1.C([BH3-])#N.[Na+]>C(O)(=O)C>[Cl:14][C:11]1[CH:12]=[C:13]2[C:8]([CH2:7][CH2:6][CH2:5][CH:4]2[NH:3][O:2][CH3:1])=[CH:9][CH:10]=1참가 물질
4
반응 조건
- 온도
- 23 °C
실험 절차
To a stirred solution of crude 7-chloro-3,4-dihydro-2H-naphthalen-1-one-O-methyl-oxime (5.9 g; 28.14 mmol) prepared as described in example P1a in acetic acid (100 ml) was added portion wise sodium cyanoborohydride 95% (3.54 g; 56.3 mmol) at 15° C. The mixture was stirred for 6 hours at 23° C. Most of acetic acid was removed under reduced pressure. The residue was poured in 2N NaOH (100 ml) and was extracted with ethylacetate (3×80 ml). Combined organics were dried over sodium sulfate and solvent was removed in vacuo. The crude (8.2 g) was subject to flash chromatography (eluant: c-hexane/ethyl acetate 90:10) to afford 2.70 g (45% of theory) of N-(7-chloro-1,2,3,4-tetrahydro-naphthalen-1-yl)-O-methyl-hydroxylamine as a yellow oil.