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 2063455Notes

Reaction equation

HRID 2063455 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>Cl.O1CCOCC1>[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-triazoleYield 118.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

De-Boc by HCl procedure: A solution of Boc-protected triazole from Example 3 (1.95 g, 5.374 mmol) in 100 mL of 4 N HCl in dioxane was stirred at room temperature for 4 h. The mixture was concentrated in vacuo and then treated with minimum amount of MeOH, diluted with ether, white crystal precipitated out. After filtration, the white crystal was collected and dried in vacuo to yield the HCl salt of desired product (1.67 g, 92.6%, yield calculated based on 2 eq. HCl attached).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additiontreated with minimum amount of MeOH
  3. additiondiluted with ether, white crystal
  4. customprecipitated out
  5. filtrationAfter filtration
  6. customthe white crystal was collected
  7. customdried in vacuo

Sources & evidence

ORD record
ord-28a18f09e336406fa25562292d990e42
Source dataset
uspto-grants-2012_10
Patent number
US08288371B2

Reaction notes

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