Methanol → [2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]methanol

HRID 1404521Notes

Reaction equation

[CH:1]1([C:4]2[C:13]([CH:14]=[O:15])=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH2:3][CH2:2]1.CO.O1CCCC1.[BH4-].[Na+]>CCCCCC.C(OCC)(=O)C.O>[CH:1]1([C:4]2[C:13]([CH2:14][OH:15])=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

2-Cyclopropyl-4-(4-fluorophenyl)quinoline-3-carbaldehyde (30 gm) was added methanol (30 ml) and tetrahydrofuran (270 ml) at room temperature. The reaction mixture was then cooled to 0° C. and then added sodium borohydride (5.8 gm) for 30 minutes at 0 to 5° C. The reaction mass was stirred for 1 hour 30 minutes and then added water (150 ml) and ethyl acetate (150 ml). The reaction mass was stirred for 10 minutes, and then the layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried with sodium sulfate and then concentrated to obtain a residual solid. To the residual solid was added n-hexane (150 ml) and stirred for 30 minutes. The separated solid was filtered and dried to obtain 29 gm of (2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)methanol.

Workup

stirringThe reaction mass was stirred for 10 minutes
customthe layers were separated
extractionthe aqueous layer was extracted with ethyl acetate
dry with materialThe combined organic layers were dried with sodium sulfate
concentrationconcentrated
customto obtain a residual solid
stirringstirred for 30 minutes
filtrationThe separated solid was filtered
customdried

Sources & evidence

ORD record: ord-94e83b968ed24290875080b6c8fbe10d
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912333B2

Reaction notes

Loading…