Ethanol → HCID 86761375, compound

HRID 1015572Notes

Reaction equation

HRID 1015572 reaction equation
[C:1]([CH2:3][C:4]12[CH2:12][CH:8]3[CH2:9][CH:10]([CH2:11]1)[C:6]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])([CH2:7]3)[CH2:5]2)#[N:2].[CH2:21]([OH:23])C.Cl.[NH2:25]O.C([O-])([O-])=O.[Na+].[Na+]>O>[O:23]1[CH:21]=[N:25][C:1]([CH2:3][C:4]23[CH2:12][CH:8]4[CH2:9][CH:10]([CH2:11]2)[C:6]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])([CH2:7]4)[CH2:5]3)=[N:2]1

Participants

6

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 86761376HCID 86761376, compound

Product 1

HCID 86761375HCID 86761375, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of the compound obtained from step I (0.25 g, 0.9 mmol) in a 1:1-mixture of ethanol and water (9 mL) at room temperature was added hydroxylamine hydrochloride (0.32 g, 4.5 mmol) followed by solid Na2CO3 (0.57 g, 5.4 mmol). The reaction mixture was refluxed for 12 h. The volatiles were removed under reduced pressure and the residue was dissolved in ethylacetate and washed with water. The organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was dissolved in trimethyl orthoformate (0.2 mL) and a catalytic amount of camphor sulfonic acid was added. The reaction mixture was refluxed for 4 h. The volatiles were removed under reduced pressure and the crude product was purified by column chromatography to obtain tert-butyl [1-(1,2,4-oxadiazol-3-ylmethyl)tricyclo[3.3.1.03,7]non-3-yl]carbamate (0.15 g) in 51% yield as viscous liquid. m/z (M+1), 320; 1H NMR (CDCl3) 300 MHz δ 8.62 (s, 1H), 4.71 (bs, 1H), 2.79 (s, 2H), 2.48-2.38 (m, 1H), 2.35-2.28 (m, 1H), 2.10-1.88 (m, 4H), 1.74 (dd, J=2.8, 10.5 Hz, 2H), 1.65-1.38 (m, 4H), 1.43 (s, (H).

Workup

  1. temperatureThe reaction mixture was refluxed for 12 h
  2. customThe volatiles were removed under reduced pressure
  3. dissolutionthe residue was dissolved in ethylacetate
  4. washwashed with water
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. customevaporated under reduced pressure
  7. dissolutionThe residue was dissolved in trimethyl orthoformate (0.2 mL)
  8. additiona catalytic amount of camphor sulfonic acid was added
  9. temperatureThe reaction mixture was refluxed for 4 h
  10. customThe volatiles were removed under reduced pressure
  11. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-95d83fe36421469ba0c9ebd84fedcf38
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

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