Trifluoroacetic acid → HCID 178448023, compound

HRID 2214323Notes

Reaction equation

FC(F)(F)C(O)=O.C([SiH](CC)CC)C.[F:15][C:16]1[CH:21]=[C:20]([C@H:22]2[CH2:27][CH2:26][C@H:25]([C@H:28]3[CH2:33][CH2:32][C@H:31]([CH2:34][CH2:35][CH3:36])[CH2:30][CH2:29]3)[CH2:24][CH2:23]2)[CH:19]=[C:18]([F:37])[C:17]=1[C:38](=O)[C@@H:39]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH3:40].[OH-].[Na+]>ClCCCl>[F:15][C:16]1[CH:21]=[C:20]([C@H:22]2[CH2:27][CH2:26][C@H:25]([C@H:28]3[CH2:29][CH2:30][C@H:31]([CH2:34][CH2:35][CH3:36])[CH2:32][CH2:33]3)[CH2:24][CH2:23]2)[CH:19]=[C:18]([F:37])[C:17]=1[CH2:38][C@@H:39]([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[CH3:40]

Participants

Conditions

Temperature: 60 °C

Procedure

Then, 5 ml of trifluoroacetic acid and 2.6 g (23 mmol) of triethylsilane were added to a 1,2-dichloroethane 8 ml solution of 4.1 g (9.1 mmol) of (R)-1-[2,6-difluoro-4-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]phenyl]-2-phenyl-1-propanone at room temperature, followed by stirring at 60° C. for 10 hours. This reaction liquid was poured into 200 ml of a 5% sodium hydroxide solution, and after extraction with toluene, washing with water, drying, distillation of the solvent, recrystallization and purification by silica gel column chromatography were carried out to obtain 2.5 g of aimed (S)-1-[2,6-difluoro-4-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]phenyl]-2-phenylpropane.

Workup

customThis reaction liquid
extractionafter extraction with toluene
washwashing with water
customdrying
distillationdistillation of the solvent, recrystallization and purification by silica gel column chromatography

Sources & evidence

ORD record: ord-57fc4218e5094a3b87de5ab7375e184e
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07108895B2

Reaction notes

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