反応 #2267085

反応方程式

sodium cyanoborohydride

2-(2,3-dihydro[1,4]oxazino[2,3,4-hi]indol-6-ylmethyl)-1H-isoindole-1,3(2H)-dione

NaOH

→

title compound

(rac)-2-(2,3,5,6-tetrahydro[1,4]oxazino[2,3,4-hi]indol-6-ylmethyl)-1H-isoindole-1,3(2H)-dione

溶媒

H2O

CH3OH

TFA

反応条件

後処理

1. 1
   抽出The mixture was then extracted with EtOAc (3×)
2. 2
   乾燥The combined EtOAc solution was dried over MgSO4
3. 3
   濃縮concentrated in vacuo to dryness
4. 4
   workup.DISSOLUTIONThe residue was redissolved in CH2Cl2
5. 5
   ろ過filtered
6. 6
   濃縮The filtrate was concentrated in vacuo to dryness

実験手順

A freshly prepared solution of sodium cyanoborohydride (0.093 g, 1.48 mmol) in CH3OH (0.3 mL) was added dropwise to a 0° C. solution of 2-(2,3-dihydro[1,4]oxazino[2,3,4-hi]indol-6-ylmethyl)-1H-isoindole-1,3(2H)-dione (0.094 g, 0.29 mmol) in TFA (3.0 mL). The mixture was stirred at rt for 1 hour and diluted with H2O (10.0 mL) and made basic by the addition of 15% NaOH. The mixture was then extracted with EtOAc (3×). The combined EtOAc solution was dried over MgSO4 and concentrated in vacuo to dryness. The residue was redissolved in CH2Cl2 and filtered. The filtrate was concentrated in vacuo to dryness and the residue was subjected to preparative TLC (EtOAc/Hex., ½) to give 0.031 g (33%) of light yellow oil as the title compound: 1H NMR (400 MHz, CDCl3) δ 7.93-7.88 (m, 2 H), 7.80-7.75 (m, 2 H), 6.79-6.77 (m, 1 H), 6.75-6.65 (m, 2 H), 4.46-4.43 (m, 2 H), 4.10-4.05 (m, 1 H), 4.00-3.94 (m, 1 H), 3.77-3.73 (m, 1 H), 3.34-3.33 (m, 1 H), 3.30-3.26 (m, 1 H), 3.17-3.15 (m, 1 H), 3.10-3.08 (m, 1 H); MS (EI) m/z 321 (M++H).

出典