Sodium borohydride → tert-Butyl 6-(hydroxymethyl)-1H-indole-1-carboxylate

HRID 551500Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 551500
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH:17]=[O:18])[CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][OH:18])[CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 14616867Tert-butyl 6-formyl-1H-indole-1-carboxylate

Produkt 1

HCID 23560816tert-Butyl 6-(hydroxymethyl)-1H-indole-1-carboxylateAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 6-formyl-indole-1-carboxylic acid tert-butyl ester (1.2 g) in methanol (5 mL) in an ice bath was added sodium borohydride (0.27 mg) portion wise. The reaction was allowed to warm to room temperature over 1.5 hr. The reaction diluted with ethyl acetate (200 mL) washed with water (200 mL), brine (100 mL), dried over sodium sulfate, concentrated, adsorbed onto silica gel and purified by flash chromatography with a gradient from 5-40% ethyl acetate in hexanes to yield 6-hydroxymethyl-indole-1-carboxylic acid tert-butyl ester as a clear viscous oil (0.91 g, 78%) LC-MS (ES) calculated for C14H17NO3, 247.1; found m/z 246 [M−H]−.

Aufarbeitung

  1. washwashed with water (200 mL), brine (100 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. custompurified by flash chromatography with a gradient from 5-40% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-9a2b0b784e274660a39d5f4ea3df2cd7
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947728B1

Notizen zur Reaktion

Wird geladen…