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Benzyl Alcohol → benzyl 2(R)-(4-methoxybenzyl)-3-(morpholinocarbonyl)propionate

HRID 2380122
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2380122
C([Li])CCC.[CH2:6]([OH:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([C@H]1COC(=O)N1[C:23](=[O:43])[C@H:24]([CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1)[CH2:25][C:26](=[O:33])[N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)(C)C.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH3:42][O:41][C:38]1[CH:37]=[CH:36][C:35]([CH2:34][C@H:24]([CH2:25][C:26]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[O:33])[C:23]([O:13][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:43])=[CH:40][CH:39]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 244Benzyl AlcoholHCID 25517Ammonium ChlorideHCID 14429470Zioaxgayzkltkq-iebwsbkvsa-HCID 178418339Butyllithium

Produkt 1

HCID 18656646benzyl 2(R)-(4-methoxybenzyl)-3-(morpholinocarbonyl)propionateAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×
HCID 8058HexaneLösungsmittel

Versuchsvorschrift

7.84 ml (12.5 mmoles) of butyllithium (as a 1.6M hexane solution) were added, whilst ice-cooling and under an atmosphere of nitrogen, to a solution of 1.73 ml (16.7 mmoles) of benzyl alcohol in 50 ml of anhydrous tetrahydrofuran. The mixture was stirred for 10 minutes, and then a solution of 3.50 g (8.36 mmoles) of 4(S)-isopropyl-3-[4-oxo-2(R)-(4-methoxybenzyl)-4-morpholinobutyryl]-2-oxazolidinone (prepared as described in Preparation 13) in 10 ml of anhydrous tetrahydrofuran was added dropwise thereto. The mixture was then stirred for 30 minutes, after which a saturated aqueous solution of ammonium chloride was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, the solvent was removed by distillation under reduced pressure, and the residue was purified by medium pressure silica gel column .chromatography (using a 4:1 by volume mixture of benzene and ethyl acetate as eluent), followed by recrystallization from diisopropyl ether, to give 3.09 g (yield 93%) of the title compound as white crystals, melting at 77°-79° C.

Aufarbeitung

  1. stirringThe mixture was then stirred for 30 minutes
  2. extractionwas then extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customthe residue was purified by medium pressure silica gel column .chromatography (
  6. additionby volume mixture of benzene and ethyl acetate as eluent),
  7. customfollowed by recrystallization from diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-7328d4d836d94b1da25532707521f78a
Quelldatensatz
uspto-grants-1994_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05364844

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