Diisopropylamine → HCID 13326773, compound

HRID 2291138Notes

Reaction equation

C(NC(C)C)(C)C.C([Li])CCC.[C:13]([CH:15]1[CH2:20][CH:19]2[CH2:21][CH2:22][CH:16]1[CH2:17][CH2:18]2)#[N:14].Br[CH2:24][CH:25]1[O:29][CH2:28][CH2:27][O:26]1>O1CCCC1>[C:13]([C:15]1([CH2:24][CH:25]2[O:29][CH2:28][CH2:27][O:26]2)[CH2:20][CH:19]2[CH2:21][CH2:22][CH:16]1[CH2:17][CH2:18]2)#[N:14]

Participants

Conditions

Temperature: -78 °C

Procedure

84 ml of diisopropylamine are dissolved in 300 ml of absolute tetrahydrofuran. 39.9 ml of n-butyllithium (1.5 molar in hexane) are added at -20° C. under dry argon. After 30 minutes at room temperature, the mixture is cooled down to -78° C. and 8.1 g of 2-cyanobicyclo[2.2.2]octane in 30 ml of absolute tetrahydrofuran are stirred in, and, after 30 minutes at 0° C., the mixture is again cooled down to -78° C. and 10 g of 2-bromomethyl-1,3-dioxolane in 30 ml of tetrahydrofuran are added dropwise. The mixture is stirred for a further 45 minutes at -78° C., warmed up to room temperature and evaporated, and the residue is taken up in 2N acetic acid and ether, washed three times with water and dried over sodium sulfate and the solvent is removed. The crude product is chromatographed on silica gel with ethyl acetate/cyclohexane (1:6) as the mobile phase. 7.9 g of the title compound are obtained as a colorless oil.

Workup

additionare added dropwise
temperaturewarmed up to room temperature
customevaporated
washether, washed three times with water
dry with materialdried over sodium sulfate
customthe solvent is removed
customThe crude product is chromatographed on silica gel with ethyl acetate/cyclohexane (1:6) as the mobile phase

Sources & evidence

ORD record: ord-1c200b28ecdb4a2196d62fb58e26f998
Source dataset: uspto-grants-1986_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04620012

Reaction notes

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