Sodium Azide → HCID 124036082, compound

HRID 1628034Notes

Reaction equation

HRID 1628034 reaction equation
CS(O[CH2:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[C:13]([O:15][CH3:16])=[O:14])(=O)=O.[N-:17]=[N+:18]=[N-:19].[Na+]>CN(C=O)C.O>[N:17]([CH2:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[C:13]([O:15][CH3:16])=[O:14])=[N+:18]=[N-:19]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 87313767HCID 87313767, compound

Product 1

HCID 124036082HCID 124036082, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (trans)-methyl 2-((methylsulfonyloxy)methyl)cyclohexanecarboxylate (1.4 g, 5.6 mmol) in DMF (6 mL) was added NaN3 (0.730 g, 11.0 mmol). The mixture was heated at about 100° C. for about 3 h. The mixture was diluted with water (30 mL) and extracted with EtOAc (2×45 mL). The combined organic layers were washed with aqueous 1 N NaOH (1×40 mL). The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give (trans)-methyl 2-(azidomethyl)cyclohexanecarboxylate (1.1 g, 100%.): 1H NMR (400 MHz, CDCL3) δ 3.69 (d, J=6.0, 3H), 3.28-3.15 (m, 2H), 2.24-2.14 (m, 1H), 1.97-1.73 (m, 5H), 1.46 (dd, J=12.2, 3.2, 1H), 1.36-1.05 (m, 3H).

Workup

  1. extractionextracted with EtOAc (2×45 mL)
  2. washThe combined organic layers were washed with aqueous 1 N NaOH (1×40 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-49efd158bc934e5d80bd1ddf3ac807df
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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