Aluminium lithium hydride → HCID 70200310, Verbindung

HRID 861353Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 861353
C[O:2][C:3]([CH2:5][C:6]1[CH:29]=[CH:28][C:9]([O:10][CH2:11][C@@H:12]2[CH2:27][N:15]3[CH2:16][CH2:17][N:18]([C:20]4[N:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=4)[CH2:19][C@@H:14]3[CH2:13]2)=[CH:8][CH:7]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[OH:2][CH2:3][CH2:5][C:6]1[CH:29]=[CH:28][C:9]([O:10][CH2:11][C@@H:12]2[CH2:27][N:15]3[CH2:16][CH2:17][N:18]([C:20]4[N:21]=[CH:22][C:23]([F:26])=[CH:24][N:25]=4)[CH2:19][C@@H:14]3[CH2:13]2)=[CH:8][CH:7]=1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 57016126HCID 57016126, Verbindung

Produkt 1

HCID 70200310HCID 70200310, VerbindungAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A solution of 0.13 g (0.33 mmol) of (7S,8aS)-7-(4-((methoxycarbonyl)methyl)phenoxy)methyl-2-(5-fluoropyrimidin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine (Example 11i) in 15 mL of anhydrous ethyl ether was added dropwise to an ice-cold suspension of 0.025 g (0.65 mmol) of lithium aluminum hydride in 15 mL of anhydrous ethyl ether and the mixture stirred for 30 min. The reaction was carefully quenched at 0° C. with 0.025 mL of water, 0.025 mL of 15% sodium hydroxide, and 0.075 mL of water. The precipiate which formed was filtered through Celite, the filtrate concentrated in vacuo, and purification of the residue by flash silica gel chromatography with 95:5 ethyl acetate:methanol gave 0.075 g (63%) of the title compound. mp (.HCl) 145°-147° C. HRMS calcd for C20H26FN4 O2 (MH+): 373.2040, found: 373.2054.

Aufarbeitung

  1. customThe reaction was carefully quenched at 0° C. with 0.025 mL of water, 0.025 mL of 15% sodium hydroxide, and 0.075 mL of water
  2. customThe precipiate which formed
  3. filtrationwas filtered through Celite
  4. concentrationthe filtrate concentrated in vacuo, and purification of the residue by flash silica gel chromatography with 95:5 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-12b82b0127504299966061e250f6691f
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05714487

Notizen zur Reaktion

Wird geladen…