Ammonium formate → HCID 57827141, compound

HRID 1842268Notes

Reaction equation

HRID 1842268 reaction equation
C([O-])=O.[NH4+].[N:5]([C@@:8]1([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[CH:16]=2)[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]1[OH:14])=[N+]=[N-]>CO.[Zn]>[NH2:5][C@@:8]1([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[CH:16]=2)[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]1[OH:14]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57827693HCID 57827693, compound

Product 1

HCID 57827141HCID 57827141, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

Ammonium formate (16.9 g) and zinc (5.25 g) were added to a solution of (±)-(3R*,4R*)-4-azido-4-(3-bromophenyl)tetrahydropyran-3-ol (16.0 g) in methanol (250 mL). The mixture was stirred at room temperature overnight, and then the excess of methanol was evaporated under reduced pressure. The residue was diluted with an ammonium chloride solution, and the aqueous layer was extracted with chloroform. The organic layer was washed with an ammonium chloride solution and brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (10.9 g).

Workup

  1. customthe excess of methanol was evaporated under reduced pressure
  2. additionThe residue was diluted with an ammonium chloride solution
  3. extractionthe aqueous layer was extracted with chloroform
  4. washThe organic layer was washed with an ammonium chloride solution and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d327220354d24ddc83e82a8376834218
Source dataset
uspto-grants-2015_02
Patent number
US08946210B2

Reaction notes

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