Water → 1''-(2-Fluoro-2-methyl-propyl)-5-(4-methylsulfonyl-phenyl)-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

HRID 2406342Notes

Reaction equation

HRID 2406342 reaction equation
COCC[S](F)(F)([F:10])CCOC.O[C:14]([CH3:44])([CH3:43])[CH2:15][N:16]1[CH2:21][CH2:20][C:19]2([CH2:24][C:23]3([O:42][C:27]4=[CH:28][N:29]=[C:30]([C:32]5[CH:37]=[CH:36][C:35]([S:38]([CH3:41])(=[O:40])=[O:39])=[CH:34][CH:33]=5)[CH:31]=[C:26]4[CH2:25]3)[CH2:22]2)[CH2:18][CH2:17]1.O>ClCCl.CO>[F:10][C:14]([CH3:44])([CH3:43])[CH2:15][N:16]1[CH2:21][CH2:20][C:19]2([CH2:24][C:23]3([O:42][C:27]4=[CH:28][N:29]=[C:30]([C:32]5[CH:37]=[CH:36][C:35]([S:38]([CH3:41])(=[O:40])=[O:39])=[CH:34][CH:33]=5)[CH:31]=[C:26]4[CH2:25]3)[CH2:22]2)[CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 962WaterHCID 867012021''-(2-Hydroxy-2-methyl-propyl)-5-(4-methylsulfonyl-phenyl)-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]HCID 178496537HCID 178496537, compound2×

Product 1

HCID 721948541''-(2-Fluoro-2-methyl-propyl)-5-(4-methylsulfonyl-phenyl)-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 6344DichloromethaneSolvent

Procedure

Bis(2-methoxyethyl)sulfur trifluoride (50% in toluene; 40 μL) is added to a solution of 1″-(2-hydroxy-2-methyl-propyl)-5-(4-methylsulfonyl-phenyl)-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1′-cyclobutane-3′,4″-piperidine] (20 mg) in dichloromethane (5 mL) chilled in an ice bath. The solution is stirred in the cooling bath for 2 h before another portion of bis(2-methoxyethyl)sulfur trifluoride (50% in toluene; 20 μL) is added. After stirring for 3 h, a few drops of methanol and water are added. The resulting solution is concentrated and the residue is purified by HPLC on reversed phase (acetonitrile/water/trifluoroacetic acid) to give the title compound as bis(trifluoroacetic acid) salt. LC (method 1): tR=0.76 min; Mass spectrum (ESI+): m/z=459 [M+H]+.

Workup

  1. temperaturechilled in an ice bath
  2. additionis added
  3. concentrationThe resulting solution is concentrated
  4. customthe residue is purified by HPLC on reversed phase (acetonitrile/water/trifluoroacetic acid)

Sources & evidence

ORD record
ord-d0e9115862fa428e8f37b4325a8ed809
Source dataset
uspto-grants-2014_08
Patent number
US08809361B2

Reaction notes

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