HCID 67357781, compound → HCID 86658114, compound

HRID 245511Notes

Reaction equation

HRID 245511 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]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[N:19][O:20][C:3]=12>ClCCl.[Mn]>[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]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[N:19][O:20][C:3]=12

Participants

4

Reactant 1

HCID 67357781HCID 67357781, compound2×

Product 1

HCID 86658114HCID 86658114, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 23930ManganeseCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of (7-chloro-6-((2R,6S)-2,6-dimethylmorpholino)-3-(pyridin-2-yl)isoxazolo[4,5-b]pyridin-5-yl)methanol (Intermediate 201, 0.39 g, 1.04 mmol) in dichloromethane (20 mL) was added Manganese dioxode (0.543 g, 6.24 mmol). The mixture was allowed to stir 2 days at room temperature. The reaction was filtered over Celite®, and the filtrate concentrated under vacuum to give clear oil. The oil was purified on short bed of silica using 20-30% acetone in n-hexane to give 0.16 g (42%) of the title compound as a yellow solid.

Workup

  1. filtrationThe reaction was filtered over Celite®
  2. concentrationthe filtrate concentrated under vacuum
  3. customto give clear oil
  4. customThe oil was purified on short bed of silica using 20-30% acetone in n-hexane

Sources & evidence

ORD record
ord-9da1059bb7894579b79ba6d0a4fec94f
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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