Sodium Azide → (1R,3S,5R)-3-Azidomethyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

HRID 1527443Notes

Reaction equation

HRID 1527443 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:13]([CH2:14]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:26]=[N+:27]=[N-:28].[Na+]>CS(C)=O.CCOCC>[C:1]([O:5][C:6]([N:8]1[C@H:13]([CH2:14][N:26]=[N+:27]=[N-:28])[CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86673858(1R,3S,5R)-3-(Toluene-4-sulfonyloxymethyl)-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

Product 1

HCID 86673859(1R,3S,5R)-3-Azidomethyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of (1R,3S,5R)-3-(toluene-4-sulfonyloxymethyl)-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester (0.400 g, 1.08 mmol) and NaN3 (0.420 g, 6.47 mmol) in dry DMSO (8 mL) was stirred at 65° C. overnight. After cooling, the mixture was diluted with Et2O and washed with water (×3) and brine (×2). The organics were dried (phase separator) and concentrated in vaccuo to give the title compound as a colorless oil. MS (LC-MS): 239.0 [M+H]+; tR (HPLC conditions k): 3.78 min. The material thus obtained was used in the next step without further purification.

Workup

  1. temperatureAfter cooling
  2. washwashed with water (×3) and brine (×2)
  3. customThe organics were dried (phase separator)
  4. concentrationconcentrated in vaccuo

Sources & evidence

ORD record
ord-e51d3cc078b94720a911f89c465556c5
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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