tert-butyl (3R,4S)-3-amino-4-(1H-1,2,3-triazol-1-yl)pyrrolidine-1-carboxylate → rac-(3R,4S)-4-(1H-1,2,3-triazol-1-yl)pyrrolidin-3-amine

HRID 1742991Notes

Reaction equation

HRID 1742991 reaction equation
[NH2:1][C@H:2]1[C@@H:6]([N:7]2[CH:11]=[CH:10][N:9]=[N:8]2)[CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1>FC(F)(F)C(O)=O>[NH2:1][C@H:2]1[C@@H:6]([N:7]2[CH:11]=[CH:10][N:9]=[N:8]2)[CH2:5][NH:4][CH2:3]1

Participants

3

Reactant 1

HCID 124582585tert-butyl (3R,4S)-3-amino-4-(1H-1,2,3-triazol-1-yl)pyrrolidine-1-carboxylate

Product 1

HCID 70283180rac-(3R,4S)-4-(1H-1,2,3-triazol-1-yl)pyrrolidin-3-amine

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of compound of example K (1.0 g) in trifluoroacetic acid (4 ml) was stirred at room temperature under nitrogen for 10 minutes and concentrated. The residue was dissolved in methanol and treated with basic resin (ANGA-316) and filtered. The filtrate was concentrated and purified by column chromatography over neutral alumina using methanol/CHCl3 mixture as solvent. Yield 670 mg. 1H NMR (CD3OD) δ: 2.80 (m, 1H), 3.20-3.80 (m, 5H), 5.10 (m, 1H), 7.75 (s, 1H), 8.0 (S, 1H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in methanol
  3. additiontreated with basic resin (ANGA-316) and
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by column chromatography over neutral alumina

Sources & evidence

ORD record
ord-15eeffc485c04b22b7075e9042f92ac5
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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