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

HRID 2074860노트

반응식

HRID 2074860 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-f13b432c2f95440ab18a2e9359f1b463
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919491B2

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