Sulfuric acid magnesium salt (1:1) → HCID 118468191, compound

HRID 629452Notes

Reaction equation

HRID 629452 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C:7]2[C:8]([CH3:20])=[C:9]([CH3:19])[C:10]([CH:17]=O)=[C:11]([CH:16]=2)[C:12](OC)=[O:13])=[CH:4][C:3]=1[O:23][CH3:24].[NH2:25][C@@H:26]1[C@@H:31]([OH:32])[CH2:30][CH2:29][O:28][CH2:27]1.S([O-])([O-])(=O)=O.[Mg+2]>C1COCC1>[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C:7]2[CH:16]=[C:11]3[C:10]([CH2:17][N:25]([C@@H:26]4[C@@H:31]([OH:32])[CH2:30][CH2:29][O:28][CH2:27]4)[C:12]3=[O:13])=[C:9]([CH3:19])[C:8]=2[CH3:20])=[CH:4][C:3]=1[O:23][CH3:24]

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 55285677(3S,4S)-3-Aminotetrahydro-2H-pyran-4-OLHCID 118468380HCID 118468380, compound

Product 1

HCID 118468191HCID 118468191, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-(4-fluoro-3-methoxybenzyl)-2-formyl-3,4-dimethylbenzoate (0.35 g) in THF (4.00 mL) were added (3S,4S)-3-aminotetrahydro-2H-pyran-4-ol (0.12 g) and anhydrous magnesium sulfate (0.26 g), and the mixture was stirred at room temperature for 5 hr under nitrogen atmosphere. The insoluble substance was removed by filtration, the filtrate was concentrated, and the residue was diluted with methanol (2.00 mL)-THF (4.00 mL). Sodium triacetoxyborohydride (0.45 g) was added thereto, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.13 g).

Workup

  1. customThe insoluble substance was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. additionthe residue was diluted with methanol (2.00 mL)-THF (4.00 mL)
  4. additionSodium triacetoxyborohydride (0.45 g) was added
  5. stirringthe mixture was stirred overnight at room temperature
  6. additionThe reaction mixture was diluted with ethyl acetate
  7. washthe mixture was washed with water and saturated brine
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-562be074b1af487fb245fbd9591cadd4
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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