Azadirachtin → 108168-76-9

HRID 359495Notes

Reaction equation

HRID 359495 reaction equation
[CH3:1]/[CH:2]=[C:3](/[C:5]([O:7][C@@H:8]1[C@:16]23[C@H:20]([C@@:21]([C@:25]45[O:30][C@@:29]4([CH3:31])[C@@H:28]4[C@:32]6([OH:38])[C@H:36]([O:37][C@H:26]5[CH2:27]4)[O:35][CH:34]=[CH:33]6)([CH3:24])[C@H:22]([OH:23])[C@H:14]4[C@H:15]2[C@:11]([C:44]([O:46][CH3:47])=[O:45])([CH2:12][O:13]4)[C@H:10]([O:48][C:49]([CH3:51])=[O:50])[CH2:9]1)[C@@:19]([OH:43])([C:39]([O:41][CH3:42])=[O:40])[O:18][CH2:17]3)=[O:6])\[CH3:4]>[Pd].C(O)C>[CH3:1][CH2:2][CH:3]([C:5]([O:7][C@@H:8]1[C@:16]23[C@H:20]([C@@:21]([C@:25]45[O:30][C@@:29]4([CH3:31])[C@@H:28]4[C@:32]6([OH:38])[C@H:36]([O:37][CH:26]5[CH2:27]4)[O:35][CH2:34][CH2:33]6)([CH3:24])[C@H:22]([OH:23])[C@H:14]4[C@H:15]2[C@:11]([C:44]([O:46][CH3:47])=[O:45])([CH2:12][O:13]4)[C@H:10]([O:48][C:49]([CH3:51])=[O:50])[CH2:9]1)[C@@:19]([OH:43])([C:39]([O:41][CH3:42])=[O:40])[O:18][CH2:17]3)=[O:6])[CH3:4]

Participants

4

Reactant 1

HCID 5281303Azadirachtin

Product 1

HCID 71300945108168-76-9Yield 59.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Azadirachtin (30 mg, 0.042 mmol) and 0.5 ml of ethanol was stirred with 20 mg of 5% palladium on alumina at 20° C. under hydrogen (10 atm) for 3 hours. The reaction mixture was then filtered and rotary evaporated in vacuo. The crude product was purified by silica gel preparative HPLC (solvent=2-propanol:n-hexane, 17:83, v/v), followed by ODS preparative HPLC (solvent=methanol:water, 1:1, v/v) to give 2',3',22,23-tetrahydroazadirachtin (18 mg).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customrotary evaporated in vacuo
  3. customThe crude product was purified by silica gel preparative HPLC (solvent=2-propanol

Sources & evidence

ORD record
ord-1a23030e2fde4f88b089973a77d45453
Source dataset
uspto-grants-1991_03
Patent number
US05001149

Reaction notes

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