Methanol → HCID 118343083, Verbindung

HRID 2202714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2202714
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:18])[C:7]=1[CH2:8][C@H:9]1[CH2:13][C:12]2([CH2:17][CH:16]=[CH:15][CH2:14]2)[CH2:11][NH:10]1.CO>CCOC(C)=O.C(Cl)Cl.[Pd]>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:18])[C:7]=1[CH2:8][C@H:9]1[CH2:13][C:12]2([CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:11][NH:10]1

Komponenten

6

Edukt 2

HCID 887MethanolHCID 118342875HCID 118342875, Verbindung

Produkt 1

HCID 118343083HCID 118343083, VerbindungAusbeute 58,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of (R)-3-((3,5-dichloropyridin-4-yl)methyl)-2-azaspiro[4.4]non-7-ene (0.090 g, 0.318 mmol) and palladium 10 wt. % on activated carbon (0.034 g, 0.032 mmol) in EtOAc (4 ml) was stirred under hydrogen balloon at room temperature for 3 h. Starting material was converted to the desired project with mono-chloro product (˜4:1). The crude material was absorbed onto a plug of silica gel and purified by chromatography through a REDISEP™ pre-packed silica gel column (12 g), eluting with a gradient of 5% to 50% 1 M NH3.MeOH in DCM, to provide (R)-3-((3,5-dichloropyridin-4-yl)methyl)-2-azaspiro[4.4]nonane (0.053 g, 0.186 mmol, 58.5% yield) as a brown oil. 1H NMR (400 MHz, CDCl3) δ 8.42-8.50 (m, 2H), 3.63-3.83 (m, 1H), 3.28 (br. s., 2H), 3.02 (d, J=10.37 Hz, 1H), 2.87 (br. s., 1H), 1.73-1.83 (m, 1H), 1.54-1.72 (m, 9H), 1.42-1.53 (m, 1H); LCMS (ESI) m/z 285.0 (M+H)+.

Aufarbeitung

  1. customThe crude material was absorbed onto a plug of silica gel
  2. custompurified by chromatography through a REDISEP™ pre-packed silica gel column (12 g)
  3. washeluting with a gradient of 5% to 50% 1 M NH3

Quellen und Nachweise

ORD-Eintrag
ord-80eba55500864439b6f1382d6782a263
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365522B2

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