Aluminium lithium hydride → HCID 73656243, compound

HRID 1885732Notes

Reaction equation

C([N:3]1[C:7]2[CH2:8][CH2:9][C:10]3[C:17]4([CH3:20])[CH:18]([CH3:19])[CH:4]1[CH2:5][C:6]=2[C:11]=3[CH:12]=[CH:13][CH2:14][N:15]=[CH:16]4)#N.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:20][C:17]12[CH:18]([CH3:19])[CH:4]3[NH:3][C:7]4=[C:6]([CH2:5]3)[C:11](=[C:10]1[CH2:9][CH2:8]4)[CH:12]=[CH:13][CH2:14][N:15]=[CH:16]2

Participants

Conditions

Temperature: 0 °C

Procedure

The nitrile (1.12 g) was dissolved in 60 ml of tetrahydrofuran and 0.80 g of lithium aluminium hydride was added, with cooling to 0° C. under nitrogen. The mixture was allowed to warm to room temperature and was then heated at reflux for 2 hr. The mixture was cooled to room temperature and 10% aqueous tetrahydrofuran was added. The mixture was filtered through anhydrous sodium sulfate and then celite. The filter cakes were washed with a mixture of triethylamine/methanol/ethyl acetate, and the filtrate was concentrated. The residue was purified by flash chromatography (alumina, triethyl amine/methanol/ether) to afford 0.70 g (69%) of 6,12-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-9H-pyrrolo[3,2-h][3]benzazocine.

Workup

temperatureto warm to room temperature
temperaturewas then heated
temperatureat reflux for 2 hr
temperatureThe mixture was cooled to room temperature
filtrationThe mixture was filtered through anhydrous sodium sulfate
washThe filter cakes were washed with a mixture of triethylamine/methanol/ethyl acetate
concentrationthe filtrate was concentrated
customThe residue was purified by flash chromatography (alumina, triethyl amine/methanol/ether)

Sources & evidence

ORD record: ord-d9b26d636e0c4a7f833985656285d92a
Source dataset: uspto-grants-1992_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05145965

Reaction notes

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