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

HRID 2256822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2256822
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]D200 -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-052fefcf890441e49384c2c1445b50a7
Quelldatensatz
uspto-grants-1997_08
Patentnummer
US05656617

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