Ammonium formate → Dihydrogenistein

HRID 402862

반응식

HRID 402862 반응식
[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

참가 물질

3

반응물 2

HCID 2723923Ammonium formateHCID 5280961Genistein

생성물 1

HCID 9838356Dihydrogenistein수율 53%

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5e691af099c445ff8e562ceb4565faab
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742141B2

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