Ethyl chloroformate → HCID 9799902, compound
Reaction equation
Cl.[C:2]([C:4]1[CH:21]=[CH:20][C:7]([O:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH:16]3[CH2:18][CH2:19][CH:13]2[CH2:14][CH2:15]3)=[CH:6][CH:5]=1)#[CH:3].[Li]CCCC.Cl[C:28]([O:30][CH2:31][CH3:32])=[O:29]>O1CCCC1>[CH:13]12[CH2:14][CH2:15][CH:16]([CH2:18][CH2:19]1)[CH2:17][N:12]2[CH2:11][CH2:10][CH2:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([C:2]#[C:3][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:21][CH:20]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In the b) route of scheme 2,2-azabicyclo[2.2.2]octane hydrochloride (isoquinuclidine hydrochloride) (8) is reacted with TMS-ethynyl-phenyl ether derivative (3) in the presence of K2CO3 and potassium iodide (KI). The resulting 2-[3-(4-ethynylphenoxy)propane-1-yl]-2-azabicyclo[2.2.2]octane (9) is treated with ethyl ether solution in saturated hydrochloride gas (HCl gas in ether) to obtain 2-[3-(4-ethynylphenoxy)propane-1-yl]-2-azabicyclo[2.2.2]octane hydrochloride (compound 10). Further, this compound 10 is treated with n-BuLi, then it is reacted with ethyl chloroformate in tetrahydrofuran (THF) to give an ethyl 4-[3-(2-azabicyclo[2.2.2]octan-2-yl)propoxy]phenylpropiolate (11), then it is treated by the same method as mentioned above to provide an ethyl 4-[3-(2-azabicyclo[2.2.2]octan-2-yl)propoxy]phenylpropiolate hydrochloride (compound 12). In case of both R1 and R2 are hydrogen and m is 0 or 2 in the compounds of general formula (1), compound 13 (m=0) and compound 14 (m=2), it is prepared by the same method of scheme 1 and a) route of scheme 2 using either a 1,2-dibromoethane or a 1,4-dibromobutane in the place of a 1-bromo-3-chloropropane. ##STR4##
Sources & evidence
- ORD record
- ord-3bcafdbab23044d88ee10e44c14364ac
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06124460
Reaction notes
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