Triethylamine → trans3-[(Methylsulfonyl)oxy]-4-(1,2,3-triazol-1-yl)-1-N-(tert-butoxy carbonyl) pyrrolidine

HRID 1742990Notes

Reaction equation

HRID 1742990 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][C@H:7]1[C@H:11]([N:12]2[CH:16]=[CH:15][N:14]=[N:13]2)[CH2:10][N:9]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:8]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:6][C@H:7]1[C@H:11]([N:12]2[CH:16]=[CH:15][N:14]=[N:13]2)[CH2:10][N:9]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:8]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86748099Rac-tert-butyl (3r,4r)-3-hydroxy-4-(1h-1,2,3-triazol-1-yl)pyrrolidine-1-carboxylate

Product 1

HCID 86748100trans3-[(Methylsulfonyl)oxy]-4-(1,2,3-triazol-1-yl)-1-N-(tert-butoxy carbonyl) pyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl sulfonyl chloride (2.84 g, 24.8 mmole) was added slowly to an ice cooled solution of trans 3-hydroxy-4-(1,2,3-triazol-1-yl)-1-N-(tert.-butoxy carbonyl) pyrrolidine (3.16 g, 12.4 mmol) and triethylamine (4.36 ml, 31.3 mmol) in dry CH2Cl2 (10 ml). The reaction mixture was stirred under N2 at room temperature for 22 hrs and washed with saturated NaHCO3 and brine solution. The dichloromethane layer was dried over Na2SO4 and concentrated to give the title product. Yield 4.0 g (97%). 1H NMR (CDCl3) δ: 1.5 (S, 9H), 3.07 (s, 3H), 4.07 (m, 4H), 5.43 (m, 2H), 7.70 (S, 1H), 7.90 (S, 1H).

Workup

  1. washwashed with saturated NaHCO3 and brine solution
  2. dry with materialThe dichloromethane layer was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-68004e40eaa2442c98c1a9e96962043b
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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