O-Methylhydroxylamine hydrochloride → HCID 91582857, compound

HRID 545577Notes

Reaction equation

HRID 545577 reaction equation
Cl.[CH3:2][O:3][NH2:4].[F:5][C:6]1[CH:7]=[C:8]([CH:31]=[CH:32][CH:33]=1)[CH2:9][N:10]1[C:22]2[CH2:21][CH2:20][C@@H:19]([NH:23][C:24](=[O:28])[CH:25]([CH3:27])[CH3:26])[CH2:18][C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[C:14]([CH:29]=O)[CH:15]=2>N1C=CC=CC=1.CCOC(C)=O>[F:5][C:6]1[CH:7]=[C:8]([CH:31]=[CH:32][CH:33]=1)[CH2:9][N:10]1[C:22]2[CH2:21][CH2:20][C@@H:19]([NH:23][C:24](=[O:28])[CH:25]([CH3:26])[CH3:27])[CH2:18][C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[C:14]([CH:29]=[N:4][O:3][CH3:2])[CH:15]=2

Participants

5

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 59161186HCID 59161186, compound

Product 1

HCID 91582857HCID 91582857, compoundYield 10.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add methoxyamine hydrochloride (613 mg, 7.34 mmol) to a solution of (R)-N-[9-(3-fluorobenzyl)-6-formyl-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-isobutyramide (Example 200) (2.40 g, 6.11 mmol) in pyridine (40 mL). Stir the reaction mixture at room temperature for 18 h. Concentrate the reaction in-vacuo and dilute with EtOAc (175 mL). Wash the organics with water (3×75 mL), dry (MgSO4), filter, and concentrate to give the crude product (2.22 g) as a brown foam. Purify the crude product on 40 g silica gel (15-80% EtOAc/hexanes) to give 261 mg (10%) of the title compound as a yellow flaky solid. Re-purify the impure fractions on 40 g silica gel (50-80% (1% (2M NH3/MeOH)/CH2Cl2)/hexanes) and combine the purified materials to give 673 mg (26%) of the title compound as a yellow flaky solid. MS (ES): m/z 422 (M+1), 420 (M−1); HPLC (Method B): Rt=7.98 min (99%).

Workup

  1. concentrationConcentrate
  2. customthe reaction in-vacuo
  3. washWash the organics with water (3×75 mL)
  4. dry with materialdry (MgSO4)
  5. filtrationfilter
  6. concentrationconcentrate
  7. customto give the crude product (2.22 g) as a brown foam
  8. customPurify the crude product on 40 g silica gel (15-80% EtOAc/hexanes)

Sources & evidence

ORD record
ord-0d3db01991b24cb9a9d01836c9441d85
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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