Potassium Carbonate → HCID 86626239, compound

HRID 391409Notes

Reaction equation

HRID 391409 reaction equation
[C:1]1(C2CCN(C([O-])=O)CC2)C=CC=CC=1.C[N:17]1[N:21]=[N:20][C:19]([C:22]2[CH:23]=[C:24]([CH:47]=[C:48]([C:50]([F:53])([F:52])[F:51])[CH:49]=2)[CH2:25][O:26][CH2:27][C:28]2([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]2)=[N:18]1.N1C(C2C=C(C=C(C(F)(F)F)C=2)COC[C:65]2([C:78]3[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=3)[CH2:70][CH2:69][N:68]([C:71]([O:73]C(C)(C)C)=[O:72])[CH2:67][CH2:66]2)=NN=N1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][N:20]1[C:19]([C:22]2[CH:23]=[C:24]([CH:47]=[C:48]([C:50]([F:51])([F:52])[F:53])[CH:49]=2)[CH2:25][O:26][CH2:27][C:28]2([C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]2)=[N:18][N:17]=[N:21]1.[C:78]1([CH:65]2[CH2:66][CH2:67][N:68]([C:71]([O-:73])=[O:72])[CH2:69][CH2:70]2)[CH:79]=[CH:80][CH:81]=[CH:82][CH:83]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 58993704HCID 58993704, compoundHCID 86626239HCID 86626239, compoundHCID 178451995HCID 178451995, compound

Product 2

HCID 58993518HCID 58993518, compoundYield 9%HCID 86626239HCID 86626239, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

tert-Butyl 443-(1-methyl-1H-tetrazol-5-yl)-5-(trifluoromethyl)benzyloxy)methyl)-4-phenylpiperidine-1-carboxylate and tert-Butyl 4-((3-(2-methyl-2H-tetrazol-5-yl)-5-(trifluoromethyl)benzyloxy)methyl)-4-phenylpiperidine-1-carboxylate. tert-Butyl 4-((3-(1H-tetrazol-5-yl)-5-(trifluoromethyl)benzyloxy)methyl)-4-phenylpiperidine-1-carboxylate (80 mg, 0.15 mmol) methyl iodide (10.0 μL, 0.15 mmol) and potassium carbonate (21.0 mg, 0.15 mmol) were combined in acetone (1.5 mL) and heated at reflux overnight. After cooling to room temperature, the mixture was filtered and concentrated. Flash chromatography on silica gel (20% ethyl acetate/hexanes) afforded tert-Butyl 4-((3-(1-methyl-1H-tetrazol-5-yl)-5-(trifluoromethyl)benzyloxy)methyl)-4-phenylpiperidine-1-carboxylate (7.0 mg, 9%) and tert-Butyl 443-(2-methyl-2H-tetrazol-5-yl)-5-(trifluoromethyl)benzyloxy)methyl)-4-phenylpiperidine-1-carboxylate (48 mg, 60%). Retention time: 4.75 min and 5.20 min. (Phenomenex C18 4.6×50 mm, 10% MeOH/90% H2O/0.1% TFA→90% MeOH/10% H2O/0.1% TFA, Gradient time=6 min., Flow rate=4 mL/min.): Mass spec.: 532.31 (MH)+ and 532.31 (MH)+ respectively.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. filtrationthe mixture was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-056ddcfff4bb4422a38d2ea368758dd9
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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