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

HRID 1741488Notes

Reaction equation

HRID 1741488 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)-methanesulfonyloxy methyl pyrrolidine(10.40 g, 25.39 mmol) and tetrabutylammonium azide (8.18 g, 28.7 mmol) in toluene (250 ml) was stirred at 80° C. for 5 hr. The reaction was cooled to room temperature and diluted with EtOAc (250 ml), 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-a76c1d20cf71478cb2387cf07c276382
Source dataset
uspto-grants-1999_10
Patent number
US05972984

Reaction notes

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