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

HRID 1974849Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1974849
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 lithiumborohydride (30 mg, 1.38 mmol) in portions with stirring. After 1 hr 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-dc7908f9d0104644897b489e1dcc7873
Quelldatensatz
uspto-grants-1994_02
Patentnummer
US05284837

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