Ethyl chloroformate → HCID 9906645, compound

HRID 1955337Notes

Reaction equation

[C:1]([C:3]1[CH:21]=[CH:20][C:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]2[C:16](=[O:17])[CH:15]3[CH2:18][CH2:19][CH:12]2[CH2:13][CH2:14]3)=[CH:5][CH:4]=1)#[CH:2].C([Li])CCC.Cl[C:28]([O:30][CH2:31][CH3:32])=[O:29]>>[O:17]=[C:16]1[CH:15]2[CH2:18][CH2:19][CH:12]([CH2:13][CH2:14]2)[N:11]1[CH2:10][CH2:9][CH2:8][O:7][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[C:2][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:21][CH:20]=1

Participants

Reactant 3

HCID 10928Ethyl chloroformate

HCID 9795781HCID 9795781, compound

HCID 178418339Butyllithium

Product 1

HCID 9906645HCID 9906645, compound

Procedure

In the a) route at scheme 2,2-azabicyclo[2.2.2]octan-3-one(isoquinuclidine-3-one) (4) is treated with sodium hydride (NaH) in DMF, then it is reacted with the intermediate as above (3) in the presence of potassium iodide to yield 2-[3-(4-ethynylphenoxy)propane-1-yl]-2-azabicyclo[2.2.2]octane-3-one (compound 5). Further, compound 5 is treated with n-butyl lithium (n-BuLi), then it is reacted with ethyl chloroformate to obtain ethyl 4-[3-(3-oxo-2-azabicyclo[2.2.2]octan-2-yl)propoxy]phenylpropiolate (compound 6). Then 4-[3-(3-oxo-2-azabicyclo[2.2.2]octan-2-yl)propoxy]phenylpropiolic acid (compound 7) is provided by the hydrolysis of compound 6 using 10% sodium hydroxide in water solution (10% NaOHaq).

Sources & evidence

ORD record: ord-bb516928bcaf4c3ea923f58d96383000
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06124460

Reaction notes

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