Hydrochloric Acid → HCID 88536646, compound

HRID 1184388Notes

Reaction equation

HRID 1184388 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=O)(C)(C)C.[ClH:16].[CH3:17][O:18][NH2:19].Cl>CO.O1CCOCC1>[ClH:16].[CH3:17][O:18]/[N:19]=[C:9]1/[C@@H:8]([NH2:7])[CH2:13][CH2:12][CH2:11][CH2:10]/1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 521874O-Methylhydroxylamine hydrochlorideHCID 1519364HCID 1519364, compound

Product 1

HCID 88536646HCID 88536646, compoundYield 127%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2.13 g ((S)-2-oxo-cyclohexyl)-carbamic acid tert-butyl ester in 10 ml methanol was added 0.46 g O-methylhydroxylamine hydrochloride and the mixture was heated to reflux for 18 h. To the resulting yellow solution was added 2.0 ml of a 4M solution of hydrochloric acid in dioxane and the mixture was refluxed for 30 min. The reaction mixture was evaporated and dried under high vacuum. The semisolid residue was triturated under acetonitrile. The solid was collected by filtration and dried to constant weight under high vacuum to yield 1.25 g of the title compound as white crystals. MS (EI): 142 (M+H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 18 h
  3. temperaturethe mixture was refluxed for 30 min
  4. customThe reaction mixture was evaporated
  5. customdried under high vacuum
  6. customThe semisolid residue was triturated under acetonitrile
  7. filtrationThe solid was collected by filtration
  8. customdried to constant weight under high vacuum

Sources & evidence

ORD record
ord-f6010f4effd04cb7adbb82d5099239b9
Source dataset
uspto-grants-2014_03
Patent number
US08669254B2

Reaction notes

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