HCID 59281211, compound → [(2R,4R,5S)-5-amino-2-benzyloxymethyl-5-(2-fluorophenyl)tetrahydropyran-4-yl]methanol

HRID 217989Notes

Reaction equation

HRID 217989 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]1[O:18][CH2:17][C@:13]2([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[NH:14][O:15][CH2:16][C@@H:12]2[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[NH2:14][C@@:13]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])[CH2:17][O:18][C@@H:10]([CH2:9][O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:11][C@H:12]1[CH2:16][OH:15]

Participants

4

Reactant 1

HCID 59281211HCID 59281211, compound

Product 1

HCID 59281193[(2R,4R,5S)-5-amino-2-benzyloxymethyl-5-(2-fluorophenyl)tetrahydropyran-4-yl]methanolYield 90.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc powder (4.36 g) was added to a solution of (3aR,5R,7aS)-5-benzyloxymethyl-7a-(2-fluorophenyl)hexahydropyrano[3,4-c]isoxazole (2.29 g) in acetic acid (50 ml), and the mixture was stirred at room temperature overnight. The insoluble matter was removed by filtration through celite, and the solvent was evaporated under reduced pressure. Ice was added to the residue, followed by neutralization with a 5 N sodium hydroxide solution. The aqueous layer was extracted with dichloromethane, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (2.08 g).

Workup

  1. customThe insoluble matter was removed by filtration through celite
  2. customthe solvent was evaporated under reduced pressure
  3. additionIce was added to the residue
  4. extractionThe aqueous layer was extracted with dichloromethane
  5. dry with materialthe organic layer was dried 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-a2313c37408545738810bcb1329912bc
Source dataset
uspto-grants-2012_06
Patent number
US08198269B2

Reaction notes

Loading…