Tetrahydrofuran → (3R,5R)-3-((R)-1-hydroxyethyl)-5-(3,4,5-trifluorophenyl)morpholine-4-carboxylic acid benzyl ester

HRID 1677090

Reaktionsgleichung

Reaktionsgleichung von HRID 1677090
C(=O)(O)[O-].[Na+].Cl[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].O1CCCC1.[F:22][C:23]1[CH:24]=[C:25]([C@H:31]2[NH:36][C@@H:35]([C@H:37]([OH:39])[CH3:38])[CH2:34][O:33][CH2:32]2)[CH:26]=[C:27]([F:30])[C:28]=1[F:29]>C(OCC)(=O)C.O>[CH2:10]([O:9][C:7]([N:36]1[C@H:31]([C:25]2[CH:24]=[C:23]([F:22])[C:28]([F:29])=[C:27]([F:30])[CH:26]=2)[CH2:32][O:33][CH2:34][C@@H:35]1[C@H:37]([OH:39])[CH3:38])=[O:8])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 10387Benzyl chloroformate2×HCID 516892Sodium BicarbonateHCID 67374002(R)-1-[(3R,5R)-5-(3,4,5-trifluorophenyl)morpholin-3-yl]ethanol

Produkt 1

HCID 67373415(3R,5R)-3-((R)-1-hydroxyethyl)-5-(3,4,5-trifluorophenyl)morpholine-4-carboxylic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Saturated sodium bicarbonate aqueous solution (20 mL) and benzyl chloroformate (1.31 mL) were added to a tetrahydrofuran (20 mL) solution of (R)-1-[(3R,5R)-5-(3,4,5-trifluorophenyl)morpholin-3-yl]ethanol (2 g). After stirring the reaction solution for 16 hours at room temperature, additional benzyl chloroformate (1.33 mL) was added, and the resultant was further stirred for 20 hours. Water and ethyl acetate were added, and the organic layer was partitioned. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed under a vacuum. The residue was purified by silica gel column chromatography (heptane/ethyl acetate), and the title compound (880 mg) was obtained. The physical property values are as follows.

Aufarbeitung

  1. stirringthe resultant was further stirred for 20 hours
  2. customthe organic layer was partitioned
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under a vacuum
  6. customThe residue was purified by silica gel column chromatography (heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c0d90e89cdf742cb928f5520b1f6b064
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008293B2

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