Water → (-)-2-(2-Amino-6-chloropurin-9-ylmethyl)-1,4-butanediol

HRID 864996Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 864996
C[O:2][C:3](=O)[CH:4]([CH2:10][N:11]1[CH:19]=[N:18][C:17]2[C:12]1=[N:13][C:14]([NH2:21])=[N:15][C:16]=2[Cl:20])[CH2:5][C:6](OC)=[O:7].[BH4-].[Li+].O>C(O)(C)(C)C>[NH2:21][C:14]1[N:13]=[C:12]2[C:17]([N:18]=[CH:19][N:11]2[CH2:10][CH:4]([CH2:5][CH2:6][OH:7])[CH2:3][OH:2])=[C:16]([Cl:20])[N:15]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 19027590Dimethyl 2-(2-amino-6-chloropurin-9-ylmethyl)succinate

Produkt 1

HCID 19027588(-)-2-(2-Amino-6-chloropurin-9-ylmethyl)-1,4-butanediolAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

To a solution of (-)-dimethyl-2-(2-amino-6-chloropurin-9-ylmethyl)succinate (enantiomeric excess 85%; 19.9 mg, 0.0607 mmol), dissolved in tert. butanol (2.0 ml) at 40° C., was added lithium borohydride (30 mg, 1.38 mmol) in portions with stirring After 1 h at ambient temperature, water (0.3 ml) was added slowly and stirring continued over night. Inorganic salts were filtered, washed carefully with tert. butanol and the solution was evaporated to dryness. Preparative thin-layer chromatography (PSC-Fertigplatten, Merck) with chloroform+methanol (5+1) as mobile phase afforded 16.5 mg (theoretical yield) of (-)-2-(2-amino-6-chloropurin-9-ylmethyl)-1,4-butanediol. [α]D20 ° -5.20°, [α]54620 -5.92° (c 0.625, ethanol). TLC on silica (chloroform+methanol 5+1): Rf 0.40, identical to that of the racemate.

Aufarbeitung

  1. stirringstirring
  2. waitcontinued over night
  3. filtrationInorganic salts were filtered
  4. washwashed carefully with tert. butanol
  5. customthe solution was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-81a85e290ed74a21adbd898cea44a784
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05565461

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