1-Butanaminium, N,N,N-tributyl-, azide → HCID 14117018, compound

HRID 1871197Notes

Reaction equation

HRID 1871197 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@H:9]1[CH2:21]OS(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:27]=[N+:28]=[N-:29].C([N+](CCCC)(CCCC)CCCC)CCC>C1(C)C=CC=CC=1.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@H:9]1[CH2:21][N:27]=[N+:28]=[N-:29])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 57432321-Butanaminium, N,N,N-tributyl-, azideHCID 18660169HCID 18660169, compound

Product 1

HCID 14117018HCID 14117018, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a flask protected by a safety screen, a solution of N-t-butoxycarbonyl-4(S)-t-butyldimethylsilyloxy-2(S)-methane-sulfonyloxy methyl pyrrolidine(10.40 g, 25.39 mmol) and tetrabutyl-ammonium azide (8.18 g, 28.7 mmol) in toluene (250 mmol was stirred at 80° C. for 5 hr. The reaction was cooled to room temperature and diluted with EtOAc (250 mn), washed with water and brine and dried (Na2SO4). The solvent was evaporated in vacuo to afford the title compound as a yellow oil which was used in the next step without furthur purification.

Workup

  1. customIn a flask protected by a safety screen
  2. washwashed with water and brine
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-3eb59e0d5d3e4169a4ee22dbb8468cd7
Source dataset
uspto-grants-2000_08
Patent number
US06103487

Reaction notes

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