Hydrochloric Acid → trans-1-benzyl-3-(3-hydroxypropyl)-5-phenyl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one

HRID 1780

Reaktionsgleichung

Reaktionsgleichung von HRID 1780
[CH2:1]([N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C@@H:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:11][C@H:10]([CH2:25][CH2:26][C:27](O)=[O:28])[C:9]1=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[Cl-].[Li+].Cl>O1CCCC1.C(OCC)(=O)C.C(O)C>[CH2:1]([N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C@@H:12]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[O:11][C@H:10]([CH2:25][CH2:26][CH2:27][OH:28])[C:9]1=[O:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 69947592trans-1-Benzyl2-oxo-5-phenyl-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-propionic acid

Produkt 1

HCID 69946778trans-1-benzyl-3-(3-hydroxypropyl)-5-phenyl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The mixture of 0.4 g of methyl ester of trans-1-benzyl2-oxo-5-phenyl-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-propionic acid obtained in Example 12, 0.16 g of sodium borohydride and 0.16 g of lithium chloride in 15 ml of tetrahydrofuran were stirred for 10 minutes at room temperature. To the resultant was added 30 ml of ethanol, which was stirred for 2 hours at 60° C. To the reaction mixture were added 100 ml of 1N hydrochloric acid and 150 ml of ethyl acetate. The ethyl acetate layer was washed with an aqueous solution of sodium hydrogencarbonate, which was dried over anhydrous magnesium sulfate, then the solvent was distilled off under reduced pressure. The residue was purified by means of a silica gel column chromatography (eluent, hexane:ethyl acetate=2:1) to give 0.19 g of trans-1-benzyl-3-(3-hydroxypropyl)-5-phenyl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one as needles, m.p. 59°-62° C.

Aufarbeitung

  1. stirringwas stirred for 2 hours at 60° C
  2. washThe ethyl acetate layer was washed with an aqueous solution of sodium hydrogencarbonate, which
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by means of a silica gel column chromatography (eluent, hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-14c74de0439b4c7ab9a7a1cfbae36b8f
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726306

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