2,2,2-Trifluoroethyl trifluoromethanesulfonate → 9-Tert-butyl 2-methyl 4-(2,2,2-trifluoroethyl)-1-oxa-4,9-diazaspiro[5.5]undecane-2,9-dicarboxylate

HRID 712955Notes

Reaction equation

FC(F)(F)S(O[CH2:7][C:8]([F:11])([F:10])[F:9])(=O)=O.[O:14]1[C:19]2([CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)[CH2:18][NH:17][CH2:16][CH:15]1[C:32]([O:34][CH3:35])=[O:33].C([O-])(O)=O.[Na+]>CCO>[F:9][C:8]([F:11])([F:10])[CH2:7][N:17]1[CH2:18][C:19]2([CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)[O:14][CH:15]([C:32]([O:34][CH3:35])=[O:33])[CH2:16]1

Participants

Conditions

Temperature: 70 °C

Procedure

2,2,2-Trifluoroethyl trifluoromethanesulfonate (164 μL, 1.06 mmol) was added to a solution of 9-tert-butyl 2-methyl 1-oxa-4,9-diazaspiro[5.5]undecane-2,9-dicarboxylate (222 mg, 0.71 mmol) and NaHCO3 (237 mg, 2.83 mmol) in anhydrous EtOH (6 mL) at room temperature. The reaction mixture was purged with argon, sealed with a cap and heated at 70° C. for 12 hours. The reaction mixture was cooled to room temperature, filtered and concentrated in vacuo. The crude material was purified by silica gel column chromatography using 0 to 30% EtOAc in DCM as eluent to yield 9-tert-butyl 2-methyl 4-(2,2,2-trifluoroethyl)-1-oxa-4,9-diazaspiro[5.5]undecane-2,9-dicarboxylate (197 mg, 68%). ESI-MS m/z calc. 410.4. found 411.5 (M+1)+; Retention time: 2.08 minutes (3 min run).

Workup

customThe reaction mixture was purged with argon
customsealed with
customa cap
temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-c36c7a8df22d4385a56dce88507e833e
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181273B2

Reaction notes

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