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Ammonium Chloride → tert-Butyl 6-cyano-4-hydroxy-spiro[chroman-2,4'-piperidine]-1'-carboxylate

HRID 1096921
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1096921
[C:1]([C:3]1[CH:4]=[C:5]2[C:22](=[CH:23][CH:24]=1)[O:21][C:8]1([CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1)[CH2:7][C:6]2=[O:25])#[N:2].[BH4-].[Na+].[NH4+].[Cl-]>CCO.C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]2[C:22](=[CH:23][CH:24]=1)[O:21][C:8]1([CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1)[CH2:7][CH:6]2[OH:25])#[N:2]
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Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 66649586Tert-butyl 6-cyano-4-oxo-3,4-dihydrospiro[1-benzopyran-2,4'-piperidine]-1'-carboxylate

Produkt 1

HCID 66649142tert-Butyl 6-cyano-4-hydroxy-spiro[chroman-2,4'-piperidine]-1'-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21873804Tetrahydrofuran ethanol
Lösungsmittel

Versuchsvorschrift

To a solution of 15 g of tert-butyl 6-cyano-4-oxospiro[chroman-2,4′-piperidine]-1′-carboxylate in 250 mL of EtOH-THF(1:4) at 0° C. was added NaBH4 portionwise, and the reaction mixture was allowed to warm up to rt. After stirring for 1 h, NH4Cl aqueous was added to the reaction mixture and the aqueous mixture was extracted with AcOEt twice. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in reduced pressure to give the intended compound as a pale yellow solid.

Aufarbeitung

  1. extractionthe aqueous mixture was extracted with AcOEt twice
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e7d84f57c9d248509eddb5e8ef418e95
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08138197B2

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