Potassium Sodium Tartrate → 2-(2-chloro-8-(2-hydroxypropan-2-yl)-6-morpholino-9H-purin-9-yl)propanal

HRID 334136ノート

反応式

HRID 334136 の反応式
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:17]([OH:20])([CH3:19])[CH3:18])[N:8]2[CH:11]([CH3:16])[C:12](OC)=[O:13])=[C:4]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[N:3]=1.[AlH4-].[Li+].[NH4+].[Cl-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1.C(Cl)Cl>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:17]([OH:20])([CH3:19])[CH3:18])[N:8]2[CH:11]([CH3:16])[CH:12]=[O:13])=[C:4]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[N:3]=1

参加物

7

反応物 4

HCID 9357Potassium Sodium TartrateHCID 25517Ammonium ChlorideHCID 28112Lithium aluminum hydrideHCID 86667354methyl 2-(2-chloro-8-(2-hydroxypropan-2-yl)-6-morpholino-9H-purin-9-yl)propanoate

生成物 1

HCID 866673552-(2-chloro-8-(2-hydroxypropan-2-yl)-6-morpholino-9H-purin-9-yl)propanal収率 62%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

Methyl 2-(2-chloro-8-(2-hydroxypropan-2-yl)-6-morpholino-9H-purin-9-yl)propanoate (1.6 g, 4.1 mmol) was dissolved in THF (30 mL) and cooled to −78° C. The reaction mixture was treated with a 1.0M solution of lithium tetrahydroaluminate in THF (8.6 mL) and stirred at −78° C. for 1 hr. A saturated solution of NH4Cl was added and the mixture was diluted with DCM. The reaction mixture was treated with a saturated solution of Rochelle's salt and stirred on high at ambient temperature for 1 hr. The layers were separated and the aqueous phase was extracted into DCM/MeOH (3×), dried over sodium sulfate, filtered, and absorbed onto celite for purification by flash chromatography to afford 2-(2-chloro-8-(2-hydroxypropan-2-yl)-6-morpholino-9H-purin-9-yl)propanal as a white foam (900 mg, 62%). LC/MS (ESI+): m/z 384 (M+H)

後処理

  1. stirringstirred on high at ambient temperature for 1 hr
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted into DCM/MeOH (3×)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customabsorbed onto celite for purification by flash chromatography

出典と根拠

ORDレコード
ord-f661988119294d6da75044dba598e857
出典データセット
uspto-grants-2014_11
特許番号
US08883799B2

反応ノート

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