Aluminium lithium hydride → 1-({2-[(2R)-4-(6-Fluoro-1-naphthyl)-2-methylpiperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-yl)methanamine

HRID 2056754Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2056754
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH:20]3[C:25]4[CH:26]=[CH:27][C:28]([C:30]#[N:31])=[CH:29][C:24]=4[CH2:23][CH2:22][O:21]3)[C@H:14]([CH3:32])[CH2:13]1)=[CH:7][CH:6]=[CH:5]2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH:20]3[C:25]4[CH:26]=[CH:27][C:28]([CH2:30][NH2:31])=[CH:29][C:24]=4[CH2:23][CH2:22][O:21]3)[C@H:14]([CH3:32])[CH2:13]1)=[CH:7][CH:6]=[CH:5]2

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 693073181-(2-[(2R)-4-(6-Fluoro-1-naphthyl)-2-methyl-piperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-carbonitrile

Produkt 1

HCID 693065261-({2-[(2R)-4-(6-Fluoro-1-naphthyl)-2-methylpiperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-yl)methanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-{2-[(2R)-4-(6-fluoro-1-naphthyl)-2-methyl-piperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-carbonitrile (0.50 g, 1.2 mmol) in dry THF (4 mL) was added lithium aluminium hydride (1M solution in THF) (1.4 mL, 1.4 mmol) and the mixture stirred overnight at room temperature. The reaction was quenched by cautious addition of 2M sodium hydroxide, then extracted into chloroform. The combined organic extracts were dried (MgSO4), filtered and evaporated in vacuo. The crude product was purified by preparative LC-MS to yield the title compound as a yellow oil. M+H=480.

Aufarbeitung

  1. customThe reaction was quenched by cautious addition of 2M sodium hydroxide
  2. extractionextracted into chloroform
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe crude product was purified by preparative LC-MS

Quellen und Nachweise

ORD-Eintrag
ord-fb79df0ecfd842799dd09c5f28df9b6b
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07335660B2

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