Sodium Azide → tert-Butyl (2S)-2-(azidomethyl)pyrrolidine-1-carboxylate

HRID 1599666Notes

Reaction equation

HRID 1599666 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])(=O)=O)=CC=1.[N-:25]=[N+:26]=[N-:27].[Na+]>CS(C)=O.CCOCC>[N:25]([CH2:12][C@@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[N+:26]=[N-:27]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 11783214tert-Butyl (2S)-2-(((4-methylbenzene-1-sulfonyl)oxy)methyl)pyrrolidine-1-carboxylate

Product 1

HCID 23520181tert-Butyl (2S)-2-(azidomethyl)pyrrolidine-1-carboxylateYield 91%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

(S)-2-[[[(4-Methylphenyl)sulfonyl]oxy]methyl]-1-pyrrolidinecarboxylic acid, 1,1-dimethylethyl ester (3.55 g, 10 mmol, see J. Das et al, J. Med Chem, 1992, Vol. 35,2610 for preparation) was dissolved in dimethyl sulfoxide (DMSO) (40 mL) and treated with sodium azide (980 mg, 15 mmol). The mixture was heated at 70° C. for 5 hours, then cooled and diluted with ether. After washing with water (3×50 mL), the ether layer was dried (MgSO4) and freed of solvent in vacuo to give title compound as a colorless oil (2.05 g, 91%) which was used without further purification.

Workup

  1. temperaturecooled
  2. washAfter washing with water (3×50 mL)
  3. dry with materialthe ether layer was dried (MgSO4)

Sources & evidence

ORD record
ord-c870eb220ac74cfebb989112920f5930
Source dataset
uspto-grants-1998_04
Patent number
US05741799

Reaction notes

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