Sodium Azide → trans-Ethyl 2-azidomethyl-1-cyclopropanecarboxylate

HRID 355240Notes

Reaction equation

HRID 355240 reaction equation
CS(O[CH2:6][C@@H:7]1[CH2:9][C@H:8]1[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=O)=O.[N-:15]=[N+:16]=[N-:17].[Na+]>CS(C)=O>[N:15]([CH2:6][C@@H:7]1[CH2:9][C@H:8]1[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N+:16]=[N-:17]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 53825740(1R,2R)-ethyl 2-((methylsulfonyloxy)methyl)cyclopropanecarboxylate

Product 1

HCID 22816282trans-Ethyl 2-azidomethyl-1-cyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The trans-ethyl 2-methanesulfonyloxymethyl-1-cyclopropanecarboxylate from the previous step (1.655 g, 7.45 mmol) was dissolved in dry dimethyl sulfoxide (20 ml), treated with sodium azide (0.969 g, 14.89 mmol), and stirred at room temperature for 16 h. (tlc indicated no substrate left). After dilution with water, (50 ml), the reaction mixture was extracted with ether (3×50 ml) and the combined organic extracts washed several times (×6) with water and then brine (×3). After drying on anhydrous magnesium sulfate, evaporation of the solvent under reduced pressure gave an oil. Bulb to bulb distillation gave a clear liquid; 1.178 g (93%); bp 86°-90° C./4.0 mm Hg (air bath temperature); ir (film) νmax : 2090 (N3), 1725 cm-1 (C=O); 1Hmr (CDCl3) δ:4.13 (2H, q, J=7, CH2 --CH3), 3.21 (2H, d, J=6, CH2 --OMs), 2.0-0.6 (4H, m, cyclopropyl), 1.23 (3H, t, 5.7, CH2 --CH3). Anal. calcd for C7H11N3O2 : C 49.69, H 6.55, N 24.83; found: C 49.81, H 6.71, N 24.29.

Workup

  1. waitno substrate left)
  2. extractionAfter dilution with water, (50 ml), the reaction mixture was extracted with ether (3×50 ml)
  3. washthe combined organic extracts washed several times (×6) with water
  4. dry with materialAfter drying on anhydrous magnesium sulfate, evaporation of the solvent under reduced pressure
  5. customgave an oil
  6. distillationBulb to bulb distillation
  7. customgave a clear liquid

Sources & evidence

ORD record
ord-7323d38b4aa548438df7374caefc9e96
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

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