Sodium Hydroxide → (8S)-octahydropyrrolo[1,2-a]pyrazin-8-ol

HRID 421213ノート

反応式

HRID 421213 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][C@@H:8]1[CH:12]2[C:13](=O)[NH:14][CH2:15][C:16](=O)[N:11]2[CH2:10][CH2:9]1.[OH-].[Na+]>C1COCC1>[CH2:13]1[NH:14][CH2:15][CH2:16][N:11]2[CH2:10][CH2:9][C@H:8]([OH:7])[CH:12]12

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59215828(8S)-8-hydroxyhexahydropyrrolo[1,2-a]pyrazine-1,4-dione

生成物 1

HCID 55300579(8S)-octahydropyrrolo[1,2-a]pyrazin-8-ol収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

Into a stirred, cooled (0° C.) suspension of LiAlH4 (3.3 g, 88 mmol) in 60 ml of dry THF, was introduced (8S)-8-hydroxyhexahydropyrrolo[1,2-a]pyrazine-1,4-dione (D70, 750 mg, 4.4 mmol) in small portions. The mixture was then allowed to reach rt and stirred for 48 h, after which it was cooled to 0° C. THF was introduced (70 ml), then successively a saturated solution of Na—K-tartrate (5 ml) and a 20% aqueous NaOH solution (5 ml) were dropped into the flask, under vigorous stirring. The suspension was stirred for 30 min at rt, and filtered. The pale filter cake was washed with 100 ml of CHCl3 and the combined filtrates and washings were evaporated in vacuo to give 500 mg of the title compound. From GC-MS analysis 2 diastereomeric products were still observed. Yield 80%.

後処理

  1. temperatureInto a stirred, cooled
  2. customto reach rt
  3. stirringThe suspension was stirred for 30 min at rt
  4. filtrationfiltered
  5. washThe pale filter cake was washed with 100 ml of CHCl3
  6. customthe combined filtrates and washings were evaporated in vacuo

出典と根拠

ORDレコード
ord-e32205eb95a848f3ad81320f659390d1
出典データセット
uspto-grants-2012_01
特許番号
US08097618B2

反応ノート

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