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

HRID 864996ノート

反応式

HRID 864996 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-81a85e290ed74a21adbd898cea44a784
出典データセット
uspto-grants-1996_10
特許番号
US05565461

反応ノート

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