6,8-Difluoro-2-tetralone → 2-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid methyl ester

HRID 505043Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505043
Cl.[CH3:2][O:3][C:4](=[O:10])[C@H:5]([CH2:7][CH2:8][CH3:9])[NH2:6].[F:11][C:12]1[CH:13]=[C:14]2[C:19](=[C:20]([F:22])[CH:21]=1)[CH2:18][C:17](=O)[CH2:16][CH2:15]2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:10])[CH:5]([NH:6][CH:17]1[CH2:16][CH2:15][C:14]2[C:19](=[C:20]([F:22])[CH:21]=[C:12]([F:11])[CH:13]=2)[CH2:18]1)[CH2:7][CH2:8][CH3:9]

Komponenten

5

Edukt 3

HCID 40764316,8-Difluoro-2-tetraloneHCID 5049666Sodium triacetoxyborohydrideHCID 14118488methyl (2S)-2-aminopentanoate hydrochloride

Produkt 1

HCID 671643272-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Combine L-norvaline methyl ester-hydrochloride (1 equiv) with 6,8-difluoro-3,4-dihydro-1H-naphthalen-2-one (1 equiv) in methylene chloride and stir 30 min. and add sodium triacetoxy borohydride (1.1 equiv) and stir at rt overnight. The reaction is quenched with aqueous sodium bicarbonate, extracted with methylene chloride, dried, and concentrated. The resultant material is purified by silica gel chromatography to afford the separated diastereomers of 2-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid methyl ester: Diastereomer 1; 13C NMR (100 MHz, CDCl3) 14.0, 19.4, 27.7, 28.2, 29.5, 29.6, 36.3, 51.1, 58.7, 100.7, 100.9, 101.2, 110.5, 110.7, 110.8, 118.5, 118.6, 141.1, 159.7, 159.8, 162.1, 176.7; MS m/z 298.3 (M+1). Diastereomer 2; Diagnostic 13C NMR (100 MHz, CDCl3) 14.0, 19.3, 28.3, 28.4, 28.5, 30.3, 36.4, 51.1, 52.0, 58.5, 100.7, 100.9, 101.2, 110.5, 110.7, 176.8; MS m/z 298.3 (M+1).

Aufarbeitung

  1. customThe reaction is quenched with aqueous sodium bicarbonate
  2. extractionextracted with methylene chloride
  3. customdried
  4. concentrationconcentrated
  5. customThe resultant material is purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0783b6865f92457aba42575fcc33b912
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781435B2

Notizen zur Reaktion

Wird geladen…