4-Hydroxybenzaldehyde → (2S,4R,5R)-2-benzhydryl-5-(4-hydroxy-benzylamino)-tetrahydropyran-4-ol

HRID 78942Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 78942
[NH2:1][C@@H:2]1[CH2:7][O:6][C@H:5]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][C@H:3]1[OH:21].[OH:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1.C(O)(=O)C.[BH3-]C#N.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.CO.O>[CH:8]([C@@H:5]1[CH2:4][C@@H:3]([OH:21])[C@H:2]([NH:1][CH2:27][C:26]2[CH:29]=[CH:30][C:23]([OH:22])=[CH:24][CH:25]=2)[CH2:7][O:6]1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

9

Edukt 5

HCID 1264-HydroxybenzaldehydeHCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 11514718(2S,4R,5R)-5-amino-2-benzhydryl-tetrahydro-pyran-4-ol

Produkt 1

HCID 11552844(2S,4R,5R)-2-benzhydryl-5-(4-hydroxy-benzylamino)-tetrahydropyran-4-ol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of (2S,4R,5R)-5-amino-2-benzhydryl-tetrahydro-pyran-4-ol 31a (0.02 g, 0.09 mmol), 4-hydroxybenzaldehyde (0.01 g, 0.09 mmol) and glacial acetic acid (0.005 g, 0.09 mmol) in 1,2-dichloroethane (5 ml) was added portionwise NaCNBH3 (0.007 g, 0.11 mmol) in methanol (1 ml). The reaction was continued for 4 hr. Water was added to quench the reaction and the mixture was stirred for 30 minutes at 0° C. The reaction mixture was stirred with saturated aqueous NaHCO3 and the product was extracted with methylene chloride (3×10 ml). The combined organic phases were washed with brine, water and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure, and the residue was purified by flash chromatography (Hexane/Ethyl Acetate/Triethylamine 3:2:0.2) to give (2S,4R,5R)-2-benzhydryl-5-(4-hydroxy-benzylamino)-tetrahydropyran-4-ol, (−)-32a, 0.03 g (80%, [α]D=(−)72.6, c=1, MeOH).

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. extractionthe product was extracted with methylene chloride (3×10 ml)
  4. washThe combined organic phases were washed with brine, water
  5. dry with materialdried over anhydrous Na2SO4
  6. customSolvent was removed under reduced pressure
  7. customthe residue was purified by flash chromatography (Hexane/Ethyl Acetate/Triethylamine 3:2:0.2)

Quellen und Nachweise

ORD-Eintrag
ord-fc3f7695c62b407ba6438aee8193d995
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841464B2

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