Sodium Azide → (3S,4S)-benzyl 3-azido-4-ethylpyrrolidine-1-carboxylate

HRID 1487306Notes

Reaction equation

HRID 1487306 reaction equation
[CH2:1]([C@@H:3]1[C@@H:7](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:6][N:5]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH2:4]1)[CH3:2].[N-:29]=[N+:30]=[N-:31].[Na+]>CN(C=O)C.O.C(OCC)(=O)C.O>[N:29]([C@H:7]1[C@@H:3]([CH2:1][CH3:2])[CH2:4][N:5]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH2:6]1)=[N+:30]=[N-:31]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 86707893(3S,4R)-benzyl 3-ethyl-4-(tosyloxy)pyrrolidine-1-carboxylate

Product 1

HCID 86707894(3S,4S)-benzyl 3-azido-4-ethylpyrrolidine-1-carboxylateYield 100.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 22728543Water ethylacetateSolvent

Procedure

(3S,4R)-Benzyl 3-ethyl-4-(tosyloxy)pyrrolidine-1-carboxylate (21.25 g, 52.7 mmol) in DMF (50 mL) was added to a solution of sodium azide (8.56 g, 132 mmol) in DMF (50 mL) and water (30 mL) and heated to a bath temp. of 100° C. overnight. The reaction mixture was diluted with ethyl acetate/water and stirred. The organic layer was washed with water, dried (Na2SO4) and concentrated to give (3S,4S)-benzyl 3-azido-4-ethylpyrrolidine-1-carboxylate (14.5 g, 52.9 mmol, 100% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 7.34-7.41 (5H, m), 5.13-5.21 (2H, m), 4.08-4.11 (1H, m), LCMS: M+23=299, t=2.15 min.

Workup

  1. temperatureheated to a bath temp
  2. customof 100° C.
  3. customovernight
  4. washThe organic layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b1ac8ec644544d31977b64425e4c7b16
Source dataset
uspto-grants-2016_08
Patent number
US09428511B2

Reaction notes

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