Ammonium formate → Dihydrogenistein

HRID 449178

反応式

HRID 449178 の反応式
[CH:1]1[C:6]([C:7]2[C:16](=[O:17])[C:15]3[C:14]([OH:18])=[CH:13][C:12]([OH:19])=[CH:11][C:10]=3[O:9][CH:8]=2)=[CH:5][CH:4]=[C:3]([OH:20])[CH:2]=1.C([O-])=O.[NH4+]>>[OH:18][C:14]1[CH:13]=[C:12]([OH:19])[CH:11]=[C:10]2[C:15]=1[C:16](=[O:17])[CH:7]([C:6]1[CH:5]=[CH:4][C:3]([OH:20])=[CH:2][CH:1]=1)[CH2:8][O:9]2

参加物

3

反応物 2

HCID 2723923Ammonium formateHCID 5280961Genistein

生成物 1

HCID 9838356Dihydrogenistein収率 53%

実験手順

Compound 22 was prepared following the general procedure described by Wähälä K. and Hase T. A., Heterocycles 28:183-86 (1989), herein incorporated by reference in its entirety. To a 50 mL round bottom flask was added genistein (270 mg, 1 mmol) and ammonium formate (1.08 g, 4 mmol). The flask was purged with N2, followed by addition of methanol (20 mL) and 10% Pd/C (255 mg). Upon consumption of the starting material (measured by reverse phase HPLC), the reaction mixture was passed through a pad of silica gel with EtOAc/Hex as the eluent. The solvent was concentrated in vacuo to afford crude 22. Purified by recrystallization from CHCl3/MeOH to afford 22 (144 mg, 53%) as brown crystals. Analytical data for isoflavanone 22: 1H NMR (500 MHz, DMSO) δ 12.19 (s, 1H), 10.84 (br s, 1H), 9.42 (br s, 1H), 7.08 (d, J=8.5 Hz, 2H), 6.73 (d, J=8.5 Hz, 2H), 5.91-5.90 (s, 2H), 4.53 (d, J=6.5 Hz, 2H), 4.00 (t, J=6.5 Hz, 1H); 13C NMR (125 MHz, DMSO) δ 197.6, 167.4, 164.6, 163.6, 157.4, 130.4, 126.3, 116.0, 102.5, 96.9, 95.5, 49.9; LCMS: Mass calculated for C15H12O5, [M+H]+, 273. Found 273.

後処理

  1. customCompound 22 was prepared
  2. customThe flask was purged with N2
  3. additionfollowed by addition of methanol (20 mL) and 10% Pd/C (255 mg)
  4. customUpon consumption of the starting material (measured by reverse phase HPLC)
  5. concentrationThe solvent was concentrated in vacuo
  6. customto afford crude 22
  7. customPurified by recrystallization from CHCl3/MeOH

出典と根拠

ORDレコード
ord-de3af3a06781475abde7cf4e47387010
出典データセット
uspto-grants-2013_07
特許番号
US08481760B2

関連ノート

読み込み中…