HCID 45116038, compound → HCID 130624317, compound

HRID 921803Notes

Reaction equation

HRID 921803 reaction equation
[OH:1][C@H:2]1[CH2:12][N:5]2[C:6](=O)[CH2:7][NH:8][C:9](=O)[C@@H:4]2[CH2:3]1>C1COCC1>[CH2:9]1[NH:8][CH2:7][CH2:6][N:5]2[CH2:12][C@H:2]([OH:1])[CH2:3][CH:4]12

Participants

3

Procedure

A solution of LiAIH4 in THF (2M in THF, 20 ml, 40 mmol) was added slowly to a solution of (+/−)-(7R,8aS)-7-hydroxyhexahydropyrrolo[1,2-a]pyrazine-1,4-dione (prepared according to a published literature procedure: Pharmaceutical Chemistry Journal, Vol 46, No. 2, 96 (2012), 2 g, 11.75 mmol) in THF (60 mL) and the resulting mixture was heated at reflux for 5 h. The reaction was quenched with careful addition of 0.6 ml of water, 0.6 ml of 15% NaOH and 1.2 ml water. Celite and anhydrous magnesium sulfate were then added and the mixture stirred for 1 h. The mixture was filtered and the filtrate was concentrated to give (+/−)-(7R)-octahydropyrrolo[1,2-a]pyrazin-7-ol (0.925 g) which was used without further purification.

Workup

  1. customprepared
  2. temperatureat reflux for 5 h
  3. customThe reaction was quenched with careful addition of 0.6 ml of water, 0.6 ml of 15% NaOH and 1.2 ml water
  4. additionCelite and anhydrous magnesium sulfate were then added
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ab49806f628b410785ce64b0dae23fc2
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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