tert-butyl N-(4-aminobutyl)carbamate → HCID 69294992, Verbindung

HRID 899676Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 899676
[C:1]([O:5][C:6]([N:8]1[C:12]2[C:13](=O)[CH2:14][CH2:15][CH2:16][C:11]=2[N:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:18]([O:22][C:23](=[O:30])[NH:24][CH2:25][CH2:26][CH2:27][CH2:28][NH2:29])([CH3:21])([CH3:20])[CH3:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]([NH:29][CH2:28][CH2:27][CH2:26][CH2:25][NH:24][C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:30])[CH2:14][CH2:15][CH2:16][C:11]=2[N:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 117842630HCID 117842630, Verbindung

Produkt 1

HCID 69294992HCID 69294992, VerbindungAusbeute 48,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 7-oxo-4,5,6,7-tetrahydorbenzoimidazole-1-carboxylic acid tert-butyl ester (632 mg, 2.82 mmol) in CH2Cl2 (50 mL) at room temperature under inert atmosphere was added (4-amino-butyl)carbamic acid tert-butyl ester (745 mg, 4.23 mmol) followed by sodium triacetoxyborohydride (896 mg, 4.23 mmol). The reaction mixture was stirred at room temperature for 17 hours. Saturated sodium bicarbonate solution (20 mL) was added and the mixture was extracted with dichloromethane (3×30 mL). The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated. The resultant material was purified by column chromatography on silica gel (20:1:1 CH2Cl2:MeOH:NH4OH) to provide the product (558 mg, 48%): 1H NMR (CDCl3): δ 1.42 (s, 9H), 1.59 (s, 9H), 1.50-1.62 (m, 4H), 1.71-1.77 (2H), 1.82-2.00 (m, 2H), 2.06 (s, 1H), 2.73-2.87 (m, 4H), 3.09-3.13 (m, 2H), 3.33 (br s, 1H), 3.75-3.80 (m, 1H), 5.01 (br s, 1H), 7.96 (s, 1H).

Aufarbeitung

  1. extractionthe mixture was extracted with dichloromethane (3×30 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resultant material was purified by column chromatography on silica gel (20:1:1 CH2Cl2:MeOH:NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-2909e2f9ce0d488e9c78f42e341151c0
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07354932B2

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