Acetylene → Rac-tert-butyl (3r,4r)-3-hydroxy-4-(1h-1,2,3-triazol-1-yl)pyrrolidine-1-carboxylate

HRID 1742989Notes

Reaction equation

HRID 1742989 reaction equation
[OH:1][C@H:2]1[C@H:6]([N:7]=[N+:8]=[N-:9])[CH2:5][N:4]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:3]1.[CH:17]#[CH:18]>CC(C)=O>[OH:1][C@H:2]1[C@H:6]([N:7]2[CH:18]=[CH:17][N:9]=[N:8]2)[CH2:5][N:4]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:3]1

Participants

4

Reactant 2

HCID 6326AcetyleneHCID 15855750Tert-butyl (3R,4R)-3-azido-4-hydroxypyrrolidine-1-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of trans 3-hydroxy-4-azido-1-N-(tert.-butoxy carbonyl)pyrrolidine (3.8 g, 17 mmol) in dry acetone (50 ml) was heated at 75°-80° C. for 40 hrs. After releasing the excess of acetylene, the reaction mixture was concentrated and the residue was purified on silica gel using ethyl acetate as eluant. Yield 3.66 g (87%) m.p. 91-93° C.; 1H NMR (CDCl3) δ: 1.46 (S, 9H), 3.25-4.25 (m, 5H), 4.83 (m, 1H), 7.63 (S, 1H), 7.70 (S, 1H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue was purified on silica gel

Sources & evidence

ORD record
ord-5dc2d18f1d9e4c96bc198e19645439c1
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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