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Ammonia → Tert-butyl 1-oxo-4-phenyl-2,8-diazaspiro[4.6]undecane-8-carboxylate

HRID 1036706
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1036706
[BH4-].[Na+].[N+:3]([CH2:6][CH:7]([C:14]1([C:28]([O:30]C)=O)[CH2:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([O-])=O.N.CCOC(C)=O>CCO.CO.Cl[Ni]Cl>[O:30]=[C:28]1[C:14]2([CH2:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[CH2:16][CH2:15]2)[CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][NH:3]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 710601881-tert-Butyl 4-methyl 4-(2-nitro-1-phenylethyl)azepane-1,4-dicarboxylate

Produkt 1

HCID 71060671Tert-butyl 1-oxo-4-phenyl-2,8-diazaspiro[4.6]undecane-8-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24385
Nickel Dichloride
Katalysator
HCID 702EthanolLösungsmittel
HCID 887MethanolLösungsmittel

Versuchsvorschrift

NaBH4 (570 mg, 15.03 mmol) in EtOH (15 ml) under nitrogen was stirred for 20 minutes and added portionwise (4 aliquots) to a cooled (ice-bath) mixture comprising 1-tert-butyl 4-methyl 4-(2-nitro-1-phenylethyl)azepane-1,4-dicarboxylate (step 2) (1.079 g, 2.504 mmol) and NiCl2 (595 mg, 2.504 mmol) in MeOH (25 ml). After stirring at RT for 1 hour, sat. ammonia solution was added (50 ml) followed by EtOAc (60 ml). The mixture was reduced in vacuo and the resulting slurry was partitioned between sat. ammonia solution and EtOAc. The organic portion was separated and the aqueous was further extracted with EtOAc. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification by chromatography on silica eluting with 1-10% MeOH in TBME afforded the title compound;

Aufarbeitung

  1. additionadded portionwise (4 aliquots) to
  2. customthe resulting slurry was partitioned between sat. ammonia solution and EtOAc
  3. customThe organic portion was separated
  4. extractionthe aqueous was further extracted with EtOAc
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customPurification by chromatography on silica eluting with 1-10% MeOH in TBME

Quellen und Nachweise

ORD-Eintrag
ord-eebdefd8b11d43c7b2b2034742ba6fa3
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08546416B2

Notizen zur Reaktion

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