Formaldehyde → 5-(1-Pyrrolidinylmethyl)-1-[4-(trifluoromethyl)phenyl]-1H-tetrazole

HRID 517753Notes

Reaction equation

HRID 517753 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:6]=O.C[Si]([N:12]=[N+:13]=[N-:14])(C)C.[F:15][C:16]([F:26])([F:25])[C:17]1[CH:22]=[CH:21][C:20]([N+:23]#[C-:24])=[CH:19][CH:18]=1>CO>[N:1]1([CH2:6][C:24]2[N:23]([C:20]3[CH:19]=[CH:18][C:17]([C:16]([F:25])([F:26])[F:15])=[CH:22][CH:21]=3)[N:14]=[N:13][N:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 31268PyrrolidineHCID 78378AzidotrimethylsilaneHCID 27594124-(Trifluoromethyl)phenyl isocyanide

Product 1

HCID 866918835-(1-Pyrrolidinylmethyl)-1-[4-(trifluoromethyl)phenyl]-1H-tetrazoleYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of pyrrolidine (0.074 mL, 0.90 mmol) and formaldehyde (37%, aqueous, 0.067 mL, 0.9 mmol) in methanol (4 mL) was stirred at room temperature for 1.5 h before adding trimethylsilyl azide (0.155 mL, 1.170 mmol) and 4-(trifluoromethyl)phenyl isocyanide (200 mg, 1.170 mmol, Fluorochem, Old Glossop, UK). After stirring for 2 days the solution was concentrated in vacuo. The resulting residue was purified using MDAP. Fractions containing product were combined and concentrated in vacuo. The resulting solid was redissolved in MeOH and passed through a 5 g NH2 ion exchange column to yield the title compound as a solid (230 mg).

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe resulting residue was purified
  3. additionFractions containing product
  4. concentrationconcentrated in vacuo
  5. dissolutionThe resulting solid was redissolved in MeOH

Sources & evidence

ORD record
ord-d299a41c73a3454592099efa1dc0145c
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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