HCID 178418361, compound → 5-(Pyrrolidin-3-yl)-2H-tetrazole

HRID 1454350Notes

Reaction equation

HRID 1454350 reaction equation
C(OC([N:11]1[CH2:15][CH2:14][CH:13]([C:16]2[NH:20][N:19]=[N:18][N:17]=2)[CH2:12]1)=O)C1C=CC=CC=1.[H][H]>[Pd].CO>[NH:11]1[CH2:15][CH2:14][CH:13]([C:16]2[NH:20][N:19]=[N:18][N:17]=2)[CH2:12]1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178525125benzyl 3-(1H-tetrazol-5-yl)pyrrolidine-1-carboxylate

Product 1

HCID 221815365-(Pyrrolidin-3-yl)-2H-tetrazole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 662 mg (2.4 mmol) of (R/S)-5-[1-benzyloxycarbonyl-pyrrolidin-3-yl]-1H-tetrazole (from Step B) and 220 mg of 10% palladium on charcoal in 5 mL of MeOH was hydrogenated at atmospheric pressure using a balloon of hydrogen for 3 h. The reaction was filtered through a pad of Celite and concentrated to afford the title compound as a white solid: 1H-NMR (500 MHz, CD3OD) δ 2.27 (m, 1H), 2.49 (m, 1H), 3.39-3.51 (m, 3H), 3.70 (m, 1H), 3.85 (m, 1H).

Workup

  1. customfor 3 h
  2. filtrationThe reaction was filtered through a pad of Celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-361e12164e7d4430823a3507cb6e5856
Source dataset
uspto-grants-2009_01
Patent number
US07479504B2

Reaction notes

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