HCID 16099404, compound → HCID 16099412, compound

HRID 1865156Notes

Reaction equation

HRID 1865156 reaction equation
[CH3:1][C@H:2]1[C:24](=[O:25])[C:23]2[C@H:12]([C@H:13]3[C@@H:21]([CH:22]=2)[C@H:20]2[C@@H:16]([CH2:17][C@@H:18]([O:26][C@@H:27]4[O:32][C@@H:31]([CH3:33])[C@H:30]([O:34][CH3:35])[C@@H:29]([O:36][CH3:37])[C@H:28]4[O:38][CH3:39])[CH2:19]2)[CH:15]=[CH:14]3)[CH2:11][C:9](=[O:10])[O:8][C@@H:7]([CH:40]2[CH2:43][CH2:42][CH2:41]2)[CH2:6][CH2:5][CH2:4][C@@H:3]1[O:44][C@@H:45]1[O:50][C@H:49]([CH3:51])[C@@H:48]([N:52]([CH3:54])[CH3:53])[CH2:47][CH2:46]1>C1(C)C=CC=CC=1.C(O)C>[CH3:1][C@H:2]1[C:24](=[O:25])[C:23]2[C@H:12]([C@H:13]3[C@@H:21]([CH:22]=2)[C@H:20]2[C@@H:16]([CH2:17][C@@H:18]([O:26][C@@H:27]4[O:32][C@@H:31]([CH3:33])[C@H:30]([O:34][CH3:35])[C@@H:29]([O:36][CH3:37])[C@H:28]4[O:38][CH3:39])[CH2:19]2)[CH2:15][CH2:14]3)[CH2:11][C:9](=[O:10])[O:8][C@@H:7]([CH:40]2[CH2:43][CH2:42][CH2:41]2)[CH2:6][CH2:5][CH2:4][C@@H:3]1[O:44][C@@H:45]1[O:50][C@H:49]([CH3:51])[C@@H:48]([N:52]([CH3:53])[CH3:54])[CH2:47][CH2:46]1

Participants

4

Reactant 1

HCID 16099404HCID 16099404, compound

Product 1

HCID 16099412HCID 16099412, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A solution of 21-desethyl-21-cyclobutyl spinosyn A (3.1 mg, 0.004 mmol) in 2 mL of toluene and 0.5 mL of ethanol was purged with a slow stream of nitrogen for 20 minutes, then 2 mg of chlorotris(triphenylphosphine) rhodium was added and the solution hydrogenated at 60° C. and 1 atm. for 16 hours. After cooling and removal of solvent, the residue was chromatographed using a 10 cm×2 cm silica gel column, eluting with 5×25 mL fractions of dichloromethane containing 0%, 2%, 3%, 4%, and 5% MeOH respectively. The product-containing fractions were combined and concentrated to give 2.1 mg of 5,6-dihydro-21-desethyl-21-cyclobutyl spinosyn A. MS M+760.

Workup

  1. customhydrogenated at 60° C.
  2. temperatureAfter cooling
  3. customremoval of solvent
  4. customthe residue was chromatographed
  5. washeluting with 5×25 mL fractions of dichloromethane containing 0%, 2%, 3%, 4%, and 5% MeOH respectively
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bdf541574a4c4da0881027786bb778ca
Source dataset
uspto-grants-2009_12
Patent number
US07626010B2

Reaction notes

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