Water → (3,5-Bis-trifluoromethyl-benzyl)-(7,8-dimethoxy-1-oxo-3,3a,4,5-tetrahydro-2-oxa-9b-aza-cyclopenta[a]naphthalen-5-yl)-carbamic Acid Methyl Ester

HRID 1071715Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1071715
C([O:3][C:4]([C@H:6]1[CH2:15][C@@H:14]([N:16]([CH2:21][C:22]2[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:23]=2)[C:17]([O:19][CH3:20])=[O:18])[C:13]2[C:8](=[CH:9][C:10]([O:38][CH3:39])=[C:11]([O:36][CH3:37])[CH:12]=2)[N:7]1[C:40](OC(CC)C)=[O:41])=O)C.[BH4-].[Na+].O>CO>[CH3:20][O:19][C:17](=[O:18])[N:16]([CH2:21][C:22]1[CH:23]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:25]=[C:26]([C:28]([F:29])([F:30])[F:31])[CH:27]=1)[CH:14]1[C:13]2[C:8](=[CH:9][C:10]([O:38][CH3:39])=[C:11]([O:36][CH3:37])[CH:12]=2)[N:7]2[C:40](=[O:41])[O:3][CH2:4][CH:6]2[CH2:15]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86592230cis-4-[(3,5-Bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-6,7-dimethoxy-3,4 dihydro-2H-quinoline-1,2-dicarboxylic acid 2-butyl ester 1-ethyl ester

Produkt 1

HCID 86756497(3,5-Bis-trifluoromethyl-benzyl)-(7,8-dimethoxy-1-oxo-3,3a,4,5-tetrahydro-2-oxa-9b-aza-cyclopenta[a]naphthalen-5-yl)-carbamic Acid Methyl EsterAusbeute 85,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of cis 4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-6,7-dimethoxy-3,4-dihydro-2H-quinoline-1,2-dicarboxylic acid 2-butyl ester 1-ethyl ester (Example 5) (100 mg, 0.15 mmol) in 8.5 mL methanol at 0° C. was added sodium borohydride (57 mg, 1.5 mmol) and the resulting mixture was stirred at room temperature for 1 h. The reaction mixture was poured into water and extracted twice with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. The residue was chromatographed using 80% ethyl acetate/hexanes to afford the title product (70 mg). 1H NMR (CDCl3) δ 1.8 (br, 1H), 2.4 (br, 1H), 3.6 (s, 3H), 6.5 (br, 1H), 7.6 (br, 2H), 7.9 (s, 1H).

Aufarbeitung

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-eecc572fbb7349aba3c62a210648cdc4
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06906082B2

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