Lithium Chloride → cis-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-acetonitrile

HRID 1809109Notes

Reaction equation

C(OC(=O)[CH:5]([C:23]#[N:24])[C:6]1[S:7][CH:8]=[C:9]([C:11]([N:13]2[C@@H:22]3[C@@H:17]([CH2:18][CH2:19][CH2:20][CH2:21]3)[CH2:16][CH2:15][CH2:14]2)=[O:12])[CH:10]=1)C.[Cl-].[Li+]>CS(C)=O.C(Cl)Cl>[N:13]1([C:11]([C:9]2[CH:10]=[C:6]([CH2:5][C:23]#[N:24])[S:7][CH:8]=2)=[O:12])[C@@H:22]2[C@@H:17]([CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:16][CH2:15][CH2:14]1

Participants

Conditions

Temperature: 160 °C

Procedure

cis-Cyano-[4-(octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-acetic acid ethyl ester (0.168 g, 0.46 mmol) and lithium chloride (0.5 mmol) were dissolved in DMSO (5 mL) and heated to 160° C. by microwave irradiation for one minute. The solution was diluted with DCM (10 mL) and washed with water. The resulting organic solution was dried and the solvent evaporated to give an oil which was purified by HPLC, eluting with 10%-98% acetonitrile in water (0.1% formic acid). The fractions containing the desired product were concentrated under vacuum to give the title compound as a colourless oil (0.025 g). LCMS m/z 289.25 [M+H]+ RT=10.02 min (Analytical Method 2).

Workup

washwashed with water
customThe resulting organic solution was dried
customthe solvent evaporated
customto give an oil which
customwas purified by HPLC
washeluting with 10%-98% acetonitrile in water (0.1% formic acid)
additionThe fractions containing the desired product
concentrationwere concentrated under vacuum

Sources & evidence

ORD record: ord-24a3398ea6a74b27a0e159e900b36397
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362008B2

Reaction notes

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