Cesium carbonate → (2S)-6-bromo-5-cyclobutoxy-1-cyclopropanecarbonyl-2-methyl-1,2,3,4-tetrahydroquinoline

HRID 1051600Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]([C:12]([CH:14]3[CH2:16][CH2:15]3)=[O:13])[C@@H:7]([CH3:17])[CH2:6][CH2:5][C:4]=2[C:3]=1[OH:18].Br[CH:20]1[CH2:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Br:1][C:2]1[C:3]([O:18][CH:20]2[CH2:23][CH2:22][CH2:21]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13])[C@@H:7]([CH3:17])[CH2:6][CH2:5]2

Participants

Conditions

Temperature: 80 °C

Procedure

A 250-mL round-bottom flask was charged with (2S)-6-bromo-1-cyclopropanecarbonyl-2-methyl-1,2,3,4-tetrahydroquinolin-5-ol (2.00 g, 6.45 mmol), bromocyclobutane (1.81 mL, 2.60 g, 19.3 mmol), cesium carbonate (6.3 g, 19.34 mmol) and acetonitrile (100 mL). The resulting mixture was stirred for 6 h at 80° C. The reaction mixture was filtered through a pad of Celite and concentrated under vacuum. The residue was purified via column chromatography on silica gel (gradient elution with 0-10% ethyl acetate-petroleum ether) to afford (2S)-6-bromo-5-cyclobutoxy-1-cyclopropanecarbonyl-2-methyl-1,2,3,4-tetrahydroquinoline (2.00 g, 85%) as a colorless oil. MS (ES, m/z): 364, 366 [M+H]+

Workup

filtrationThe reaction mixture was filtered through a pad of Celite
concentrationconcentrated under vacuum
customThe residue was purified via column chromatography on silica gel (gradient elution with 0-10% ethyl acetate-petroleum ether)

Sources & evidence

ORD record: ord-c487cdb51c0e489d8618f660ed26daaa
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388161B2

Reaction notes

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