Benzylamine → (2s,3r)-Isopropyl 3-(allyloxy)-4-(benzylamino)-2-((6-(2,5-dimethyl-1h-pyrrol-1-yl)-4-methylpyridin-2-yl)methyl)butanoate

HRID 1942945

Reaktionsgleichung

Reaktionsgleichung von HRID 1942945
[CH2:1]([O:4][C@@H:5]([CH:28]=O)[C@H:6]([CH2:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([N:21]2[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]2[CH3:27])[N:15]=1)[C:7]([O:9][CH:10]([CH3:12])[CH3:11])=[O:8])[CH:2]=[CH2:3].[CH2:30]([NH2:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1COCC1>[CH2:1]([O:4][C@@H:5]([CH2:28][NH:37][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C@H:6]([CH2:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([N:21]2[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]2[CH3:27])[N:15]=1)[C:7]([O:9][CH:10]([CH3:11])[CH3:12])=[O:8])[CH:2]=[CH2:3]

Komponenten

4

Edukt 2

HCID 7504BenzylamineHCID 44543305(2S,3R)-Isopropyl 3-(allyloxy)-2-((6-(2,5-dimethyl-1H-pyrrol-1-yl)-4-methylpyridin-2-yl)methyl)-4-oxobutanoate

Produkt 1

HCID 59582524(2s,3r)-Isopropyl 3-(allyloxy)-4-(benzylamino)-2-((6-(2,5-dimethyl-1h-pyrrol-1-yl)-4-methylpyridin-2-yl)methyl)butanoateAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 16 (240 mg, 0.6 mmol) in THF (5 mL) was added benzylamine (100 μL, 0.9 mmol) followed by NaHB(OAc)3 (153 mg, 0.72 mmol). The reaction was allowed to stir for an additional 3 h then partitioned between EtOAc (100 mL) and brine (50 mL). The aqueous layer was extracted with EtOAc (50 mL). The combined organic layers were dried over Na2SO4 and concentrated. The crude product was purified by flash column chromatography (EtOAc:hexanes, 1:2-1:1) to give 19 (270 mg, 0.55 mmol, 92%) as a colorless oil: 1H NMR (500 MHz, CDCl3) δ 0.99-1.01 (d, J=6.5 Hz, 3H), 1.09-1.11 (d, J=6.5 Hz, 3H), 2.13 (s, 6H), 2.37 (s, 3H), 2.76-2.85 (ddd, J=4.5, 5.0, 12.5, Hz, 1H), 2.98-3.08 (ddd, J=5.5, 14.0, 15.5, Hz, 1H), 3.49-3.52 (m, 1H), 3.81 (s, 2H), 3.82-3.89 (m, 1H), 4.04-4.08 (dd, J=6.0, 12.5, Hz, 1H), 4.09-4.12 ((dd, J=5.5, 13.0, Hz, 1H), 4.86-4.89 (m, 1H), 5.13-5.15 (dd, J=1.0, 10.0, Hz, 1H), 5.23-5.28 (dd, J=1.5, 17.0, Hz, 1H), 5.86-5.91 (m, 3H), 6.85 (s, 1H), 7.00 (s, 1H), 7.20-7.27 (m, 2H), 7.27-7.35 (m, 3H); 13C NMR (125 MHz, CDCl3) δ 13.6, 21.2, 21.8, 21.9, 35.1, 47.6, 49.9, 54.0, 68.0, 71.4, 79.4, 106.8, 117.2, 120.3, 123.4, 127.2, 128.4, 128.6, 128.8, 134.9, 140.4, 149.5, 151.7, 159.4, 173.0; LCQ-MS (M+H+) calcd for C30H40N3O3 490. found 490; LC-TOF-MS (M+H+) calcd for C30H40N3O3 490.30697. found 490.30644.

Aufarbeitung

  1. customthen partitioned between EtOAc (100 mL) and brine (50 mL)
  2. extractionThe aqueous layer was extracted with EtOAc (50 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by flash column chromatography (EtOAc:hexanes, 1:2-1:1)

Quellen und Nachweise

ORD-Eintrag
ord-f4c6423c31654b4d85cd361928d98803
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389731B2

Verknüpfte Notizen

Wird geladen…