Chloroform → HCID 23369613, compound

HRID 1900754Notes

Reaction equation

Br[CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]3.[CH3:18][C@H:19]([NH2:30])[C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1.C(Cl)(Cl)Cl>CO>[CH3:15][C:13]1[CH:14]=[C:5]2[CH2:4][CH:3]([CH2:2][NH:30][CH:19]([C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=[CH:22][CH:21]=3)[CH3:18])[O:17][C:6]2=[C:7]2[C:12]=1[NH:11][C:10](=[O:16])[CH:9]=[CH:8]2

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 2-bromomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (1.48 g, 5.04 mmol) and S-(-)-1-(1-naphthyl)ethylamine (1.75 g, 10.2 mmol) was stirred in a hot bath at 150° C. for 3 hours. The reaction product was subjected to silica gel column chromatography (developer=chloroform: methanol=50:1) to obtain 1.78 g (91.9%) of a crude target material as a mixture of 2 types of diastereomers which are different at the position C-2. This product was further subjected to silica gel column chromatography (developer=chloroform: methanol=100:1), and the first eluted fraction was condensed under reduced pressure. As a result, 535 mg of a first diastereomer of the title compound was obtained as pale yellow powder (27.6%)

Workup

customto obtain 1.78 g (91.9%) of a crude target material
additionas a mixture of 2 types of diastereomers which
customcondensed under reduced pressure

Sources & evidence

ORD record: ord-35a32b1d124144ca94417ae24322984e
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05576324

Reaction notes

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