Sodium Hydroxide → (1aS,7bS)-2,2-Dimethyl-1a,7b-dihydro-2H-oxireno[2,3-c]chromene-6-carbonitrile

HRID 704776Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 704776
[OH-].[Na+].C(OC(N[C@@H](C)C([O:17][C@H:18]1[C:23]2[CH:24]=[C:25]([C:28]#[N:29])[CH:26]=[CH:27][C:22]=2[O:21][C:20]([CH3:31])([CH3:30])[C@@H:19]1Br)=O)=O)C1C=CC=CC=1>O.O1CCOCC1>[O:17]1[C@@H:18]2[C@H:19]1[C:20]([CH3:30])([CH3:31])[O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][C:23]=12

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 18643511(3R,4S)-4-{(2S)-2-benzyloxycarbonylaminopropionyloxy}-3-bromo-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

Produkt 1

HCID 9837089(1aS,7bS)-2,2-Dimethyl-1a,7b-dihydro-2H-oxireno[2,3-c]chromene-6-carbonitrileAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of sodium hydroxide (0.672 g) in water (16 ml) was added dropwise to a stirred solution of (3R,4S)-4-{(2S)-2-benzyloxycarbonylaminopropionyloxy}-3-bromo-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (3.896 g) in 1,4-dioxane (24 ml). After being stirred at ambient temperature for 1 hour, the mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The crystalline residue was washed with isopropyl ether and dried to give (3S,4S)-3,4-epoxy-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (1.401 g).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. washThe crystalline residue was washed with isopropyl ether
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-602ec3827b6642d982cfd269fadfc365
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04988723

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