Benzyl Alcohol → 3-Benzyloxycarbonylamino-3-(1-methylallyl)piperidine-1-carboxylic acid tert-butyl ester

HRID 1912390Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1912390
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([CH:17]([CH3:20])[CH:18]=[CH2:19])(C(O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:23]([CH2:26]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:35])C=CC=CC=1.[CH2:45]([OH:52])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1.C(OCC)(=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([NH:23][C:26]([O:52][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[O:35])([CH:17]([CH3:20])[CH:18]=[CH2:19])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

9

Edukt 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 582932773-(1-Methylallyl)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester

Produkt 1

HCID 582933873-Benzyloxycarbonylamino-3-(1-methylallyl)piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of an optically-active compound of 3-(1-methylallyl)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester (1.02 g) and triethylamine (967 μl) in toluene (10 ml) heated to 90° C. was added dropwise diphenylphosphoryl azide (1.1 ml). The reaction mixture was stirred at the same temperature for 1 hour, and then thereto were added benzyl alcohol (718 μl) and 4-dimethylaminopyridine (127 mg). The mixture was stirred with refluxing overnight, then cooled to room temperature, and thereto were added water and ethyl acetate. The separated aqueous layer was extracted with ethyl acetate twice, and the combined organic layer was washed with water twice and saturated aqueous sodium chloride solution once, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: chloroform/acetone=50/1). The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=20/1 to 4/1) to give the titled compound (845 mg).

Aufarbeitung

  1. stirringThe mixture was stirred
  2. temperaturewith refluxing overnight
  3. extractionThe separated aqueous layer was extracted with ethyl acetate twice
  4. washthe combined organic layer was washed with water twice
  5. dry with materialsaturated aqueous sodium chloride solution once, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: chloroform/acetone=50/1)
  8. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=20/1 to 4/1)

Quellen und Nachweise

ORD-Eintrag
ord-b7940fd0801f43509a27b1082300dd37
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609647B2

Notizen zur Reaktion

Wird geladen…