Sodium borohydride → (2-Hydroxymethyl-6-oxo-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indol-8-yl)carbamic Acid tert-butyl Ester

HRID 1064203Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1064203
[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:9]=[C:10]2[C:22](=[O:23])[NH:21][N:20]=[CH:19][C:12]3=[C:13]([CH:17]=[O:18])[NH:14][C:15]([CH:16]=1)=[C:11]23)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:9]=[C:10]2[C:22](=[O:23])[NH:21][N:20]=[CH:19][C:12]3=[C:13]([CH2:17][OH:18])[NH:14][C:15]([CH:16]=1)=[C:11]23)([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 178452623HCID 178452623, Verbindung

Produkt 1

HCID 136141750(2-Hydroxymethyl-6-oxo-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indol-8-yl)carbamic Acid tert-butyl EsterAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of intermediate 230(a) of Example 230 (26 mg, 0.079 mmol) in methanol (2 mL) was treated with NaBH4 (6 mg, 0.16 mmol) at 0° C. for 15 min. The solution was quenched with saturated aqueous NH4Cl and diluted with ethyl acetate. After extraction, the organic phase was washed with brine, dried (Na2SO4), filtered, and concentrated. Silica gel chromatography of the residue (3:1 ethyl acetate:hexane) gave intermediate 241(a) (13 mg) in 50% yield.

Aufarbeitung

  1. customThe solution was quenched with saturated aqueous NH4Cl
  2. additiondiluted with ethyl acetate
  3. extractionAfter extraction
  4. washthe organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f415be7797e74dcaaef5b13573cf0eaa
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06967198B2

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