Diisopropylamine → HCID 86752154, compound

HRID 863691Notes

Reaction equation

C([Li])CCC.C(NC(C)C)(C)C.[C:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH3:14].[CH2:21]1[C:31]2=[C:32]3[C:27](=[CH:28][CH:29]=[CH:30]2)[CH2:26][CH2:25][C:24](=O)[N:23]3[CH2:22]1.B(F)(F)F.CCOCC.N1CCCC1>CCCCCC.O1CCCC1>[CH2:21]1[C:31]2=[C:32]3[C:27](=[CH:28][CH:29]=[CH:30]2)[CH2:26][CH2:25]/[C:24](=[CH:14]\[C:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])/[N:23]3[CH2:22]1

Participants

Conditions

Temperature: -78 °C

Procedure

25 ml of a 1.6M solution of n-butyllithium in n-hexane were added to a solution of 4.04 g of diisopropylamine in 20 ml of tetrahydrofuran at 0° C. under nitrogen. After 10 minutes, the stirred solution was cooled to -78° C. and a solution of 9.28 g of t-butyl acetate in 20 ml of tetrahydrofuran was added. After 10 minutes, 3.46 g of 1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one in 20 ml of tetrahydrofuran was added followed by 8 ml of boron trifluoride diethyl etherate. The mixture was stirred at -78° C. and then 20 ml of pyrrolidine were added. The mixture was partitioned between ethyl acetate and water and the organic extracts were washed with water and sodium chloride solution, dried and evaporated. The residue was purified by chromatography on silica gel with ethyl acetate/petroleum ether (1:3). There were obtained 4.1 g of t-butyl (E)-(1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-ylidene)acetate of melting point 105°-107° C.

Workup

waitAfter 10 minutes
customThe mixture was partitioned between ethyl acetate and water
washthe organic extracts were washed with water and sodium chloride solution
customdried
customevaporated
customThe residue was purified by chromatography on silica gel with ethyl acetate/petroleum ether (1:3)

Sources & evidence

ORD record: ord-395162783591483bb88470e8e7ba23e8
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05721245

Reaction notes

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