Water → 10-Benzyl-3,10-diazabicyclo[4.3.1]decane

HRID 1912339Notes

Reaction equation

[CH2:1]([N:8]1[CH:14]2[CH2:15][CH2:16][CH2:17][CH:9]1[CH2:10][NH:11][C:12](=O)[CH2:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1.ClCCl>[CH2:1]([N:8]1[CH:14]2[CH2:15][CH2:16][CH2:17][CH:9]1[CH2:10][NH:11][CH2:12][CH2:13]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution obtained by dissolving 0.50 g of 10-benzyl-3,10-diazabicyclo[4.3.1]decan-4-one (1py1) in THF (4 ml) is dripped in a suspension of LiAlH4 (0.19 g) in anhydrous THF (9 ml), cooled at 0° C., kept under an argon inert atmosphere. The mixture is kept under stirring at room temperature for 14 hours. At the end the mixture is cooled to 0° C. About 0.9 ml of H2O are cautiously added while stirring for 10 min. A precipitate is obtained which is filtered under vacuum and washed with dichloromethane. The recovered filtrate is evaporated, obtaining an oil which is dissolved in dichloromethane. The organic solution is dehydrated with sodium sulphate and the solvent then evaporated. 0.47 g of the compound 10-benzyl-3,10-diazabicyclo[4.3.1]decane are recovered. Yield: quantitative; Rf: 0.62 (CH2Cl2-MeOH 8:2); 1H-NMR (CDCl3): δ (ppm) 1.17-2.18 (m, 8H), 2.62 (bs, 1H), 2.76-2.92 (m, 2H), 2.99-3.18 (m, 4H), 3.97 (s, 2H), 7.20-7.42 (m, 5H).

Workup

customA solution obtained
temperatureAt the end the mixture is cooled to 0° C
stirringwhile stirring for 10 min
customA precipitate is obtained which
filtrationis filtered under vacuum
washwashed with dichloromethane
customThe recovered filtrate is evaporated
customobtaining an oil which
customthe solvent then evaporated
custom0.47 g of the compound 10-benzyl-3,10-diazabicyclo[4.3.1]decane are recovered

Sources & evidence

ORD record: ord-038f332a90af4106abb3d7f44c0cf0c5
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609659B2

Reaction notes

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