Sodium Azide → (S)-5-(2-azido-ethyl)-2,2,4,4-tetramethyl-[1,3]dioxolane

HRID 1807061Notes

Reaction equation

HRID 1807061 reaction equation
[CH3:1][C:2]1([CH3:16])[O:6][C@@H:5]([CH2:7][CH2:8]OS(C)(=O)=O)[C:4]([CH3:15])([CH3:14])[O:3]1.[N-:17]=[N+:18]=[N-:19].[Na+]>CN(C)C=O>[N:17]([CH2:8][CH2:7][C@@H:5]1[O:6][C:2]([CH3:16])([CH3:1])[O:3][C:4]1([CH3:15])[CH3:14])=[N+:18]=[N-:19]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86640453methanesulfonic acid 2-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-ethyl ester

Product 1

HCID 86640454(S)-5-(2-azido-ethyl)-2,2,4,4-tetramethyl-[1,3]dioxolaneYield 81.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

Step H To a solution of methanesulfonic acid 2-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-ethyl ester (2.5 g, 9.9 mmol) in N,N-dimethylformamide (50 mL) was added NaN3 (6 g, 70 mmol). The reaction mixture was heated at 95° C. for 4 h. Then the mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with water, brine several times, dried over MgSO4, concentrated to give (S)-5-(2-azido-ethyl)-2,2,4,4-tetramethyl-[1,3]dioxolane as a yellow oil (1.6 g, 80%).

Workup

  1. customThen the mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with water, brine several times
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-018630b73eee41abacd1db14ac765373
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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