Aluminium lithium hydride → (4R)-4-Hydroxy-1-methyl-2-[2-(2-phenylethyl)phenoxymethyl]pyrrolidine

HRID 743300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 743300
C(O[C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][CH:9]1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:13][C@H:11]1[CH2:12][N:8]([CH3:6])[CH:9]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:10]1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 54118331(4R)-1-t-butoxycarbonyl-4-hydroxy-2-[2-(2-phenylethyl)phenoxymethyl]pyrrolidine

Produkt 1

HCID 54021671(4R)-4-Hydroxy-1-methyl-2-[2-(2-phenylethyl)phenoxymethyl]pyrrolidineAusbeute 63,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Following a procedure similar to that described in Example 38, 300 mg of (4R)-1-t-butoxycarbonyl-4-hydroxy-2-[2-(2-phenylethyl)phenoxymethyl]pyrrolidine [prepared as described in Example 65(b)] were reacted with 85.9 mg of lithium aluminum hydride dispersed in 30 ml of tetrahydrofuran. The mixture was then worked up as described in Example 38, and the crude product thus obtained was purified by column chromatography through silica gel, using a 10:1 by volume mixture of methylene chloride and methanol as the eluent, to give 150 mg (yield 63%) of the title compound as a colorless oil.

Aufarbeitung

  1. customthe crude product thus obtained
  2. customwas purified by column chromatography through silica gel
  3. additionby volume mixture of methylene chloride and methanol as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-82557143a4c44b10af182ae7deaecac3
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05556864

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