2,2,2-Trifluoroethyl trifluoromethanesulfonate → HCID 70872528, compound

HRID 712945Notes

Reaction equation

HRID 712945 reaction equation
[C:1]1([CH:7]2[O:24][C:11]3([CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(O)=O.[Na+].FC(F)(F)S(O[CH2:36][C:37]([F:40])([F:39])[F:38])(=O)=O>C(O)C>[C:1]1([CH:7]2[O:24][C:11]3([CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:13][CH2:12]3)[CH2:10][N:9]([CH2:36][C:37]([F:40])([F:39])[F:38])[CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 516892Sodium BicarbonateHCID 68291603Tert-butyl 2-phenyl-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

Product 1

HCID 70872528HCID 70872528, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To tert-butyl 10-phenyl-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate (0.98 g, 2.93 mmol) and NaHCO3 (0.99 g, 11.73 mmol) in ethanol at room temperature was added 2,2,2-trifluoroethyl trifluoromethanesulfonate (0.82 g, 545 μL, 3.52 mmol) and the reaction mixture was heated at 80° C. for 6 hours. The reaction mixture was cooled, the solid precipitate was removed by filtration and the solvent was removed in vacuo. The residue was taken up in DCM and washed sequentially with 1:1 NaOH(1N):NaHCO3 and then brine. The organics were separated, dried over sodium sulfate and concentrated in vacuo to give tert-butyl 10-phenyl-8-(2,2,2-trifluoroethyl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate (1.15 g, 95%). ESI-MS m/z calc. 414.2. found 415.3 (M+1)+; Retention time: 2.46 minutes (3 min run). 1H NMR (400 MHz, CDCl3) δ 7.44-7.26 (m, 5H), 4.81 (dd, J=10.5, 2.6 Hz, 1H), 3.73 (s, 2H), 3.31 (s, 1H), 3.09 (s, 1H), 2.98 (m, 3H), 2.74 (dd, J=11.0, 1.5 Hz, 1H), 2.51 (d, J=14.1 Hz, 1H), 2.40-2.29 (m, 2H), 1.58 (s, 3H), 1.44 (s, 9H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solid precipitate was removed by filtration
  3. customthe solvent was removed in vacuo
  4. washwashed sequentially with 1:1 NaOH(1N)
  5. customThe organics were separated
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5b5bf43adf7a45459e2222446d7ae31c
Source dataset
uspto-grants-2015_11
Patent number
US09181273B2

Reaction notes

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