HCID 67433810, compound → HCID 86658116, compound

HRID 577973Notes

Reaction equation

HRID 577973 reaction equation
[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][C@H:12]([CH3:14])[O:11][C@H:10]([CH3:15])[CH2:9]2)=[C:6]([CH2:16][OH:17])[N:5]=[C:4]2[C:18]([CH3:21])=[N:19][O:20][C:3]=12>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][C@H:12]([CH3:14])[O:11][C@H:10]([CH3:15])[CH2:9]2)=[C:6]([CH:16]=[O:17])[N:5]=[C:4]2[C:18]([CH3:21])=[N:19][O:20][C:3]=12

Participants

4

Reactant 1

HCID 67433810HCID 67433810, compound2×

Product 1

HCID 86658116HCID 86658116, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

(7-Chloro-6-((2R,6S)-2,6-dimethylmorpholino)-3-methylisoxazolo[4,5-b]pyridin-5-yl)methanol (Intermediate 352, 459 mg, 1.47 mmol) was dissolved in about 10 ml CH2Cl2. Manganese dioxide (1920 mg, 22.08 mmol) was added, and the slurry was stirred at room temperature for three days. The mixture was filtered through celite and concentrated. The crude was purified by chromatography on SiO2 using 10-30% EtOAc/hexanes. Recovered a yellow solid, 185 mg (41%).

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationconcentrated
  3. customThe crude was purified by chromatography on SiO2 using 10-30% EtOAc/hexanes
  4. customRecovered a yellow solid, 185 mg (41%)

Sources & evidence

ORD record
ord-f8ceacbadff649a79ccd68baf0b0e380
Source dataset
uspto-grants-2015_05
Patent number
US09040528B2

Reaction notes

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