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

HRID 909016Notes

Reaction equation

HRID 909016 reaction equation
[CH3:1][C:2]1([CH3:14])[O:6][C@@H:5]([CH2:7][CH2:8]OS(C)(=O)=O)[CH2:4][O:3]1.[N-:15]=[N+:16]=[N-:17].[Na+]>CN(C)C=O>[N:15]([CH2:8][CH2:7][C@H:5]1[CH2:4][O:3][C:2]([CH3:14])([CH3:1])[O:6]1)=[N+:16]=[N-:17]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 13194537methanesulfonic acid 2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester

Product 1

HCID 11457936(S)-4-(2-azido-ethyl)-2,2-dimethyl-[1,3]dioxolaneYield 88.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methanesulfonic acid 2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester (31.7 g, 0.14 mol) in N,N-dimethylformamide (200 mL) was added NaN3 (46 g, 0.71 mol). The reaction mixture was stirred at room temperature for 70 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)-4-(2-azido-ethyl)-2,2-dimethyl-[1,3]dioxolane as a yellow oil (21.3 g, 88%).

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-3b79d0d998534dfb9211cb7665088b3e
Source dataset
uspto-grants-2011_09
Patent number
US08017607B2

Reaction notes

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