Water → rel-(3aR,6aS)-Octahydro-2-(phenylmethyl)pyrrolo(3,4-c)pyrrole

HRID 857165Notes

Reaction equation

Cl.[CH2:2]([N:9]1[C:16](=O)[C@@H:15]2[C@@H:11]([CH2:12][NH:13][CH2:14]2)[C:10]1=O)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH2:2]([N:9]1[CH2:10][C@@H:11]2[C@@H:15]([CH2:14][NH:13][CH2:12]2)[CH2:16]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-Benzyl-3,7-diazabicyclo[3.3.0]octan-2,4-dione hydrochloride (73.8 g, 275 mmol; from step (b) above) was added in portions to a suspension of LiAlH4 (83.5 g, 2.26 mol) in THF at 0° C. The reaction was slowly warmed to reflux. After refluxing for 16 h the reaction was cooled to 0° C. To the cold reaction there was added dropwise sequentially H2O (84 mL), 3 M NaOH (84 mL) and H2O (250 mL). The reaction was then stirred for an additional 15 minutes and filtered through a pad of Celite® to remove the inorganic salts. The filtrate was concentrated in vacuo to afford the crude product. Kugelrohr distillation (95–115° C./66.5 Pa (0.5 mm Hg)) provided 46.8 g (84%) of the sub-title compound as a colourless oil.

Workup

temperatureThe reaction was slowly warmed to reflux
temperatureAfter refluxing for 16 h the reaction
customTo the cold reaction there
filtrationfiltered through a pad of Celite®
customto remove the inorganic salts
concentrationThe filtrate was concentrated in vacuo
customto afford the crude product
distillationKugelrohr distillation (95–115° C./66.5 Pa (0.5 mm Hg))

Sources & evidence

ORD record: ord-531c541ce57140d3aaf53c2fd271cacf
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07144914B2

Reaction notes

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