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

HRID 2245431Notes

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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%.

Workup

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

Sources & evidence

ORD record: ord-c1930c300cc743889eeb1662c2f84fcb
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07683056B2

Reaction notes

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