Formaldehyde → 3-[2-Benzyl-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidin-1-yl]-3-pyridyl]ethynyl-1-methyl-3-piperidinol

HRID 2216373Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2216373
[CH2:1]([C:8]1[C:13]([C:14]#[C:15][C:16]2([OH:22])[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]2)=[CH:12][CH:11]=[C:10]([N:23]2[CH2:27][C@@H:26]([O:28][CH3:29])[C@H:25]([OH:30])[CH2:24]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[C:33](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:1]([C:8]1[C:13]([C:14]#[C:15][C:16]2([OH:22])[CH2:21][CH2:20][CH2:19][N:18]([CH3:33])[CH2:17]2)=[CH:12][CH:11]=[C:10]([N:23]2[CH2:27][C@@H:26]([O:28][CH3:29])[C@H:25]([OH:30])[CH2:24]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 98015133-[2-Benzyl-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidin-1-yl]-3-pyridyl]ethynyl-3-piperidinol

Produkt 1

HCID 102737293-[2-Benzyl-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidin-1-yl]-3-pyridyl]ethynyl-1-methyl-3-piperidinolAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 94.0 mg of 3-[2-Benzyl-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidin-1-yl]-3-pyridyl]ethynyl-3-piperidinol (Example 1), 34.6 μl of an aqueous solution of 37% formaldehyde and 1.5 ml of dichloromethane was added 73.4 mg of sodium triacetoxyborohydride under ice-cooling, followed by stirring at room temperature for 30 minutes. The organic layer was separated by adding water and ethyl acetate to the reaction mixture, and then it was washed with an aqueous sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and the solvent was removed. The residue was purified by NH-silica gel column chromatography with 5% methanol/ethyl acetate, to give 79.0 mg of the title compound.

Aufarbeitung

  1. temperaturecooling
  2. customThe organic layer was separated
  3. additionby adding water and ethyl acetate to the reaction mixture
  4. washit was washed with an aqueous sodium hydrogen carbonate solution and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed
  7. customThe residue was purified by NH-silica gel column chromatography with 5% methanol/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-63d012b9370d4bfc8a38bdf549ded32d
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07112593B2

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