Sodium triacetoxyborohydride → HCID 11352263, Verbindung

HRID 479361Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 479361
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([NH:13][CH2:14][CH2:15][CH3:16])[CH2:10]2)=[CH:5][CH:4]=1.[C:17]([O:21][C:22]([N:24]1[CH2:30][CH2:29][C:28](=[O:31])[N:27]([CH2:32][CH2:33][CH2:34][CH:35]=O)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[C:17]([O:21][C:22]([N:24]1[CH2:30][CH2:29][C:28](=[O:31])[N:27]([CH2:32][CH2:33][CH2:34][CH2:35][N:13]([CH:9]2[CH2:8][CH2:7][C:6]3[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH2:10]2)[CH2:14][CH2:15][CH3:16])[CH2:26][CH2:25]1)=[O:23])([CH3:18])([CH3:19])[CH3:20]

Komponenten

4

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 100821727-methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amineHCID 113121495-Oxo-4-(4-oxobutyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 11352263HCID 11352263, Verbindung

Versuchsvorschrift

To a solution of (7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amine prepared as described in Example 1 (800 mg, 3.3 mmol, 1 eq) in 1,2-dichlororethane (40 mL) under inert atmosphere was added 5-oxo-4-(4-oxo-butyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (1.0 g, 3.6 mmol, 1.1 eq.) in a single portion followed by the sodium triacetoxyborohydride (1.7 g, 8.25 mmol, 2.5 eq.). The reaction was stirred at room temperature for 20 hr, concentrated in-vacuo and then partitioned between 10% KOH (50 mL) and ethyl acetate (100 mL). The organic layer was washed with brine, dried (MgSO4) and concentrated. Purification by silica gel chromatography gave 1.1 g of 4-{4-[(7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-butyl}-5 -oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester.

Aufarbeitung

  1. concentrationconcentrated in-vacuo
  2. custompartitioned between 10% KOH (50 mL) and ethyl acetate (100 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c7b7b0598ba04c7896e8cc20547e3201
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06645958B2

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