Methyl morpholine oxide → HCID 89618670, compound

HRID 926737Notes

Reaction equation

HRID 926737 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21]C(C(N3CC(=C)C3)=O)=[C:16]2[CH:15]=1.[CH3:30][N+:31]1([O-])[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1.C1[CH2:42][O:41]CC1.[OH2:43]>C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21][C:33]([C:32]([N:31]3[CH2:30][C:35]([OH:34])([CH2:42][OH:41])[CH2:36]3)=[O:43])=[C:16]2[CH:15]=1

Participants

6

Reactant 3

HCID 82029Methyl morpholine oxideHCID 21881883Oxolane--water (1/1)HCID 89618795HCID 89618795, compound

Product 1

HCID 89618670HCID 89618670, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

(R)-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyridin-3-yl)(3-methyleneazetidin-1-yl)methanone (50 mg, 0.125 mmol) and 4-methylmorpholine N-oxide (44 mg, 0.379 mmol) were dissolved in THF/Water (4:1, 2.0 ml) followed by the addition of Osmium tetroxide (1.38 mg, 0.006 mmol). Reaction mass was stirred for 16 h at 25° C., diluted with ethyl acetate and the organic layer was washed with water, NaOCl solution, followed by brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the title product as brown solid. MS (ESI): m/z 429.7 (M+H).

Workup

  1. customReaction mass
  2. washthe organic layer was washed with water, NaOCl solution
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-047ccfa86ee2448cbd75d3fd3895618f
Source dataset
uspto-grants-2016_03
Patent number
US09289419B2

Reaction notes

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