O-Methylhydroxylamine hydrochloride → HCID 86596365, compound

HRID 1272165Notes

Reaction equation

HRID 1272165 reaction equation
C(OC([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH:22]=O)=[C:14]([F:24])[CH:13]=3)[CH2:9]1)=O)(C)(C)C.Cl.[CH3:26][O:27][NH2:28]>C(O)C>[NH3:8].[CH3:26][O:27][N:28]=[CH:22][C:15]1[N:16]=[C:17]2[C:12](=[CH:13][C:14]=1[F:24])[CH2:11][C@H:10]1[N:18]2[C@H:19]([CH3:21])[CH2:20][NH:8][CH2:9]1

Participants

5

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 86596366HCID 86596366, compound

Product 2

HCID 222AmmoniaHCID 86596365HCID 86596365, compoundYield 145.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.047 g (4R,9aR)-7-fluoro-6-formyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 1 mL ethanol was added 0.014 g O-methylhydroxylamine hydrochloride and the mixture was stirred at ambient for 18 temperature for 18 h. The reaction mixture was partitioned between water and ethyl acetate. The organic phase was washed with 10% citric acid, 10% sodium bicarbonate and brine, then concentrated and purified by chromatography on silica gel with heptane:ethyl acetate=2:1. The product was treated with 1 mL trifluoroacetic acid at room temperature for 30 min. The solvent was evaporated and the residue was purified by chromatography on silica gel with dichloromethane:methanol:satd. ammonia (9:1:0.1) to yield 0.027 g (4R,9aR)-7-fluoro-4-methyl-1,2,3,4,9,9a-hexahydro-2,4a,5-triaza-fluorene-6-carbaldehyde O-methyl-oxime as a light yellow solid.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. washThe organic phase was washed with 10% citric acid, 10% sodium bicarbonate and brine
  3. concentrationconcentrated
  4. custompurified by chromatography on silica gel with heptane
  5. additionThe product was treated with 1 mL trifluoroacetic acid at room temperature for 30 min
  6. customThe solvent was evaporated
  7. customthe residue was purified by chromatography on silica gel with dichloromethane

Sources & evidence

ORD record
ord-6fee3f7fb22946cb9e1fb6c88b73bbbd
Source dataset
uspto-grants-2007_04
Patent number
US07208494B2

Reaction notes

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