Methyl morpholine oxide → HCID 59516234, compound

HRID 1160417Notes

Reaction equation

HRID 1160417 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([N:10]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[C@H:11]2[CH2:15][C:14](=[O:16])[N:13](CC=C)[CH2:12]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C[N+]1([O-])CC[O:32]CC1.C1COCC1.[CH3:41][C:42]([OH:45])(C)[CH3:43].O>[Os](=O)(=O)(=O)=O.CC(O)(C)C>[Cl:1][C:2]1[CH:9]=[C:8]([N:10]([C@H:11]2[CH2:15][C:14](=[O:16])[N:13]([CH2:41][CH:42]([OH:45])[CH2:43][OH:32])[CH2:12]2)[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 82029Methyl morpholine oxideHCID 22124471t-Butanol tetrahydrofuran waterHCID 595161582-Chloro-4-{[(2-methylphenyl)methyl][(3S)-5-oxo-1-(2-propen-1-yl)-3-pyrrolidinyl]amino}benzonitrile

Product 1

HCID 59516234HCID 59516234, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 87401860HCID 87401860, compoundCatalyst

Procedure

2-Chloro-4-{[(2-methylphenyl)methyl][(3S)-5-oxo-1-(2-propen-1-yl)-3-pyrrolidinyl]amino}benzonitrile (30.0 mg, 0.08 mmol) and 4-methyl morpholine oxide (37.5 mg, 0.16 mmol) were dissolved in a mixture of THF/t-BuOH/H2O (0.5 mL/0.2 mL/0.1 mL). To this solution was added an osmium tetroxide/2-methyl-2-propanol solution (2.5 wt %, 81.3 mg, 0.008 mmol), and the mixture stirred at room temperature for 18 h. The reaction mixture was quenched with 5% NaHSO3 (2 mL), and the organic layer was separated and concentrated to afford the desired product as a white solid (12.0 mg, 37% yield). LC-MS (ES) m/e 413.7 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with 5% NaHSO3 (2 mL)
  2. customthe organic layer was separated
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-421e9c68d58246d89c56f7654b2c3323
Source dataset
uspto-grants-2010_10
Patent number
US07816395B2

Reaction notes

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