Sodium cyanoborohydride → 8-tert-Butyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one

HRID 1879672

Reaktionsgleichung

Reaktionsgleichung von HRID 1879672
[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[C:14](=[O:15])[NH:13][CH2:12][CH:11]=[N:10][C:9]=2[CH:16]=1)([CH3:4])([CH3:3])[CH3:2].C([BH3-])#N.[Na+]>CO>[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[C:14](=[O:15])[NH:13][CH2:12][CH2:11][NH:10][C:9]=2[CH:16]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 5003444Sodium cyanoborohydrideHCID 667720198-tert-Butyl-3,4-dihydro-benzo[e][1,4]diazepin-5-one

Produkt 1

HCID 595485328-tert-Butyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

275 mg 8-tert-Butyl-3,4-dihydro-benzo[e][1,4]diazepin-5-one was dissolved in 5 mL methanol. Sodium cyanoborohydride (139 mg, 2 mmol, 2 eq) was added and the reaction was stirred for 16 hours. The reaction was quenched with water, extracted ethyl acetate 3×, washed saturated sodium bicarbonate, brine, and dried over MgSO4. Solvent was removed under vacuum and the residue chromatographed over silica gel eluting with 80% to 100% ethyl acetate in hexanes to give the title compound, 98 mg, (M+H)+=219.

Aufarbeitung

  1. customThe reaction was quenched with water
  2. extractionextracted ethyl acetate 3×
  3. washwashed saturated sodium bicarbonate, brine
  4. dry with materialdried over MgSO4
  5. customSolvent was removed under vacuum
  6. customthe residue chromatographed over silica gel eluting with 80% to 100% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-ee7a087bc4ec4d19b182c295aa8fb90f
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318719B2

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