tert-Butyl (2R)-2-{4-[(4-chlorophenyl)methyl]-4H-1,2,4-triazol-3-yl}pyrrolidine-1-carboxylate → 4-[(4-Chlorophenyl)methyl]-3-[(2R)-pyrrolidin-2-yl]-4H-1,2,4-triazole

HRID 2063454Notes

Reaction equation

HRID 2063454 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[CH:11]=[N:10][N:9]=[C:8]2[C@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2C(OC(C)(C)C)=O)=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[CH:11]=[N:10][N:9]=[C:8]2[C@H:12]2[CH2:16][CH2:15][CH2:14][NH:13]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 53486874tert-Butyl (2R)-2-{4-[(4-chlorophenyl)methyl]-4H-1,2,4-triazol-3-yl}pyrrolidine-1-carboxylate

Product 1

HCID 534868734-[(4-Chlorophenyl)methyl]-3-[(2R)-pyrrolidin-2-yl]-4H-1,2,4-triazole

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent2×

Procedure

De-Boc by TFA procedure: A solution of Boc-protected triazole from Example 3 (0.35 g, 0.9645 mmol) in 10 mL of TFA and 10 mL of CH2Cl2 was stirred at room temperature for 2 h. The mixture was concentrated in vacuo and then treated with saturated aqueous Na2CO3 (30 mL), extracted with CH2Cl2 (4×40 mL), dried over Na2SO4, and concentrated in vacuo. The desired product was obtained as a pale yellow oil (0.13 g, 51.3%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additiontreated with saturated aqueous Na2CO3 (30 mL)
  3. extractionextracted with CH2Cl2 (4×40 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6c0c1d42b49b4d0abfb790fac31fd987
Source dataset
uspto-grants-2012_10
Patent number
US08288371B2

Reaction notes

Loading…