Tetrabutylammonium Fluoride → HCID 44201118, compound

HRID 2388439Notes

Reaction equation

[Si]([O:8][C@H:9]([CH3:38])[C@@H:10]([NH:24][C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[C:27]([C:33]([F:36])([F:35])[F:34])[C:26]=1[CH3:37])[C:11]1[O:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=2)=[N:14][N:15]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:22]([C:19]1[CH:18]=[CH:17][C:16]([C:13]2[O:12][C:11]([C@H:10]([NH:24][C:25]3[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[C:27]([C:33]([F:34])([F:36])[F:35])[C:26]=3[CH3:37])[C@H:9]([OH:8])[CH3:38])=[N:15][N:14]=2)=[CH:21][CH:20]=1)#[N:23]

Participants

Conditions

Temperature: -55 °C

Procedure

4-((1R,2R)-2-(tert-butyldimethylsilyloxy)-1-(5-(4-cyanophenyl)-1,3,4-oxadiazol-2-yl)propylamino)-3-methyl-2-(trifluoromethyl)benzonitrile (500 mg, 0.92 mmol) was dissolved in THF and cooled to −55° C. under N2 atmosphere. TBAF (1.0M solution in THF, 1.10 mL, 1.11 mmol) was added to the precooled solution slowly and the temperature was allowed to rise. The progress of the reaction was monitored by TLC. After the reaction was complete, it was quenched with a saturated solution of NH4Cl and extracted with EtOAc. Purification with column chromatography provided the desired product (270 mg, 68%). 1H NMR(400 MHz, acetone-d6, δ in ppm): 8.17 (d, J=9 Hz, 2H), 7.96 (d, J=9 Hz, 2H), 7.60 (d, J=9 Hz, 1H), 7.15 (d, J=9 Hz, 1H), 6.01 (d, J=9 Hz, 1H), 5.13 (m, 1H), 4.69 (d, J=6 Hz, 1H), 4.53 (m, 1H), 2.35 (m, 3H), 1.39 (d, J=6 Hz, 3H).

Workup

customit was quenched with a saturated solution of NH4Cl
extractionextracted with EtOAc
customPurification with column chromatography

Sources & evidence

ORD record: ord-d9e0f3f4b3304e449c8dc57fdfbbe8fb
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268872B2

Reaction notes

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