Ammonium nitrate → HCID 70664206, compound

HRID 407189Notes

Reaction equation

HRID 407189 reaction equation
[CH:1]12[N:7]([C:8]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])[CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2]2.[N+]([O-])([O-])=O.[NH4+].[CH3:23][S-:24].[Na+].C1OCCOCCOCCOCCOC1>C1COCC1>[CH3:23][S:24][C@@H:6]1[CH2:5][CH2:4][CH2:3][CH2:2][C@H:1]1[NH:7][C:8](=[O:9])[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 22985Ammonium nitrateHCID 3633615-Crown-5HCID 4378561Sodium methanethiolateHCID 71441559Benzyl 7-azabicyclo[4.1.0]heptane-7-carboxylate

Product 1

HCID 70664206HCID 70664206, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl 7-azabicyclo[4.1.0]heptane-7-carboxylate (see Example 13, 0.273 g, 1.18 mmol) in 3 mL of THF was added eerie ammonium nitrate (0.065 g, 0.12 mmol) and sodium thiomethoxide (0.165 g, 2.36 mmol). After 30 min, 15-crown-5 (0.520 g, 2.36 mmol) was added. After 110 h, the reaction was concentrated in vacuo, diluted with water, and extracted 3× with diethyl ether. The combined organic fractions were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-15% ethyl acetate in hexanes to provide benzyl rac-[(1R,2R)-2-(methylthio)cyclohexyl]carbamate that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 280.1 for [M+H]+.

Workup

  1. waitAfter 110 h
  2. concentrationthe reaction was concentrated in vacuo
  3. additiondiluted with water
  4. extractionextracted 3× with diethyl ether
  5. dry with materialThe combined organic fractions were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified via silica gel chromatography
  9. washeluting with 0-15% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-5542f4b8182b41349d8a0267a407511d
Source dataset
uspto-grants-2014_06
Patent number
US08754220B2

Reaction notes

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