HCID 59587921, compound → HCID 44595147, compound

HRID 1808909Notes

Reaction equation

HRID 1808909 reaction equation
[N:1]([C@@H:4]1[C@@H:8]([O:9][CH2:10][C:11]#[CH:12])[CH2:7][N:6]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:5]1)=[N+:2]=[N-:3]>C1(C)C=CC=CC=1>[N:2]1[N:1]2[C@H:4]3[CH2:5][N:6]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7][C@@H:8]3[O:9][CH2:10][C:11]2=[CH:12][N:3]=1

Participants

3

Reactant 1

HCID 59587921HCID 59587921, compound

Product 1

HCID 44595147HCID 44595147, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (3S,4S)-tert-butyl 3-azido-4-(prop-2-ynyloxy)pyrrolidine-1-carboxylate (77 mg, 0.29 mmol) in toluene (5 ml) was heated at 120° C. for 16 hours or until TLC analysis shows completed reaction. The solvent was removed under reduced pressure and the residue was purified by flash chromatography, silica gel, gradient hexane:ethyl acetate (3:1) to neat ethyl acetate, to afford the titled compound (74 mg, 96%) as white solid. M.p. 155-157° C.

Workup

  1. customreaction
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by flash chromatography, silica gel, gradient hexane:ethyl acetate (3:1) to neat ethyl acetate

Sources & evidence

ORD record
ord-34f109b2fe3542a19384ee287f36ecb0
Source dataset
uspto-grants-2013_01
Patent number
US08362011B2

Reaction notes

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