Water → HCID 89525502, compound

HRID 2271509Notes

Reaction equation

HRID 2271509 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]([CH:10]([CH:17]1[CH2:22][CH2:21][S:20][CH2:19][CH2:18]1)[C:11]1[O:12][C:13]([CH3:16])=[CH:14][CH:15]=1)=[N+]=[N-].O.[OH-].[Na+]>O1CCCC1.C(OCC)C>[CH3:16][C:13]1[O:12][C:11]([CH:10]([NH2:7])[CH:17]2[CH2:18][CH2:19][S:20][CH2:21][CH2:22]2)=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 89525524HCID 89525524, compound

Product 1

HCID 89525502HCID 89525502, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

304 mg (8 mmol, 2 eq) of lithium aluminum hydride were added to a solution of 968 mg (4 mmol, 1 eq) of 2-[azido(tetrahydrothiopyran-4-yl)methyl]-5-methylfuran in 10 ml of tetrahydrofuran cooled to −10° C. The reaction medium was stirred at ambient temperature for 2 hours. The reaction medium was cooled to 0° C. and water with a solution of sodium hydroxide at 2 N and diethyl ether were added (precipitation of the aluminum and lithium salts). The reaction medium was filtered through celite and then the filtrate was treated with a 3 N hydrochloric acid solution. The aqueous phase was recovered and basified with a 15 N sodium hydroxide solution and then extracted with diethyl ether. The organic phases were combined, dried over magnesium sulfate, filtered and evaporated. 728 mg of C-(5-methylfuran-2-yl)-C-(tetrahydrothiopyran-4-yl)methylamine were obtained. Yield=86%.

Workup

  1. temperatureThe reaction medium was cooled to 0° C.
  2. customprecipitation of the aluminum and lithium salts)
  3. filtrationThe reaction medium was filtered through celite
  4. additionthe filtrate was treated with a 3 N hydrochloric acid solution
  5. customThe aqueous phase was recovered
  6. extractionextracted with diethyl ether
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-3994cf4c284e4d7581f723e6ef7f853a
Source dataset
uspto-grants-2015_09
Patent number
US09120772B2

Reaction notes

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