Réaction #160198

Équation de réaction

2,2-difluoroethyl trifluoromethanesulfonate

[10-(4-chlorophenyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone

NaHCO3

→

[10-(4-chlorophenyl)-8-(2,2-difluoroethyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone

Rendement 106.5%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   AutreThe reaction mixture was purged with argon
2. 2
   Autresealed with
3. 3
   Autrea cap
4. 4
   TempératureThe reaction mixture was cooled to room temperature
5. 5
   workup.ADDITIONdiluted with MeOH to 1 mL
6. 6
   Autremicrofiltered and purified by Waters mass

Mode opératoire

2,2-difluoroethyl trifluoromethanesulfonate (17 mg, 0.08 mmol) was added to a solution of [10-(4-chlorophenyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone (22 mg, 0.05 mmol) and NaHCO3 (13 mg, 0.15 mmol) in anhydrous ethanol (0.3 mL) at room temperature. The reaction mixture was purged with argon, sealed with a cap and heated at 70° C. for 40 minutes. The reaction mixture was cooled to room temperature, diluted with MeOH to 1 mL, microfiltered and purified by Waters mass directed LC/MS: (10-99% ACN/H2O (5 mM HCl)) to yield [10-(4-chlorophenyl)-8-(2,2-difluoroethyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone (27 mg, 100%). ESI-MS m/z calc. 506.21478. Found 507.2 (M+1)+; Retention time: 2.17 minutes (3 min run).

Source