(6-((2R,6S)-2,6-dimethylmorpholino)-7-fluoro-3-methylbenzo[d]isoxazol-5-yl)methanol → 6-((2R,6S)-2,6-dimethylmorpholino)-7-fluoro-3-methylbenzo[d]isoxazole-5-carbaldehyde

HRID 245371Notes

Reaction equation

HRID 245371 reaction equation
[CH3:1][C@@H:2]1[CH2:7][N:6]([C:8]2[C:17]([CH2:18][OH:19])=[CH:16][C:11]3[C:12]([CH3:15])=[N:13][O:14][C:10]=3[C:9]=2[F:20])[CH2:5][C@H:4]([CH3:21])[O:3]1>C(Cl)Cl.O=[Mn]=O>[CH3:21][C@@H:4]1[CH2:5][N:6]([C:8]2[C:17]([CH:18]=[O:19])=[CH:16][C:11]3[C:12]([CH3:15])=[N:13][O:14][C:10]=3[C:9]=2[F:20])[CH2:7][C@H:2]([CH3:1])[O:3]1

Participants

4

Reactant 1

HCID 67358969(6-((2R,6S)-2,6-dimethylmorpholino)-7-fluoro-3-methylbenzo[d]isoxazol-5-yl)methanol2×

Product 1

HCID 866580566-((2R,6S)-2,6-dimethylmorpholino)-7-fluoro-3-methylbenzo[d]isoxazole-5-carbaldehydeYield 85%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (6-((2R,6S)-2,6-dimethylmorpholino)-7-fluoro-3-methylbenzo[d]isoxazol-5-yl)methanol (Intermediate 33, 0.65 g, 2.21 mmol) in CH2Cl2 (30 ml) was added MnO2 (3.84 g, 44.17 mmol). After stirring for 3 days at room temperature MnO2 was filtered and washed with CH2Cl2. The filtrate was concentrated and dried to give the title compound (0.547 g, 85%).

Workup

  1. filtrationwas filtered
  2. washwashed with CH2Cl2
  3. concentrationThe filtrate was concentrated
  4. customdried

Sources & evidence

ORD record
ord-f8a332cb3fb846109df228ed255d04a0
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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