Water → 8-Benzyl-3,8-diazabicyclo[3.2.1]octane

HRID 1394075Notes

Reaction equation

[CH2:1]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[C:10](=O)[NH:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH2:1]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][NH:11][CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

8-Benzyl-3,8-diazabicyclo[3.2.1]octan-2-one (5.87 g, 27.1 mmol) in dry tetrahydrofuran (40 mL) was treated with 1M lithium aluminum hydride in THF (81.4 mL), heated at 60° C. for 2 hours, and then allowed to cool to room temperature and stir overnight. The mixture was cooled to 0° C. and treated in succession with water (4.4 mL), tetrahydrofuran (200 mL), 15% sodium hydroxide solution (4.4 mL), and water (13.3 mL). The mixture was filtered and the filter cake was rinsed with ethyl acetate. The filtrate was concentrated under reduced pressure to provide the title compound. MS (DCI/NH3) m/z: 203 (M+H)+.

Workup

temperatureto cool to room temperature
temperatureThe mixture was cooled to 0° C.
filtrationThe mixture was filtered
washthe filter cake was rinsed with ethyl acetate
concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-6541db5665204de687e2c82f11ea6370
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348343B2

Reaction notes

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