Sodium Azide → HCID 21070649, compound

HRID 1435349Notes

Reaction equation

HRID 1435349 reaction equation
Br[CH:2]1[CH2:7][CH2:6][N:5]([S:8]([CH3:11])(=[O:10])=[O:9])[CH2:4][CH:3]1[OH:12].[N-:13]=[N+:14]=[N-:15].[Na+]>CN(C)C=O>[N:13]([CH:2]1[CH2:7][CH2:6][N:5]([S:8]([CH3:11])(=[O:10])=[O:9])[CH2:4][CH:3]1[OH:12])=[N+:14]=[N-:15]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 13042967HCID 13042967, compound

Product 1

HCID 21070649HCID 21070649, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
84 °C

Procedure

To a stirred solution of the bromide (70 mg, 0.27 mmol, Example 307) in dimethylformamide (3 mL), sodium azide (80 mg, 1.23 mmol) was added and the mixture was stirred at 84° C. overnight. The solvent was removed and the residue was chromatographed (50% ethyl acetate/hexanej to give the desired product as a colorless oil. 51 mg, 86%. H1NMR (300MHz, CDCl3), ppm: 1.60-1.70 (m), 1 H; 2.05-2.20(m), 1 H; 2.80-3.05 (m), 2 H; 2.83 (s), 3H; 3.10 (br), 1 H (OH); 3.40-3.51 (m), 1 H; 3.51-3.62 (m), 1 H. 3.65-3.80 (m), 2 H.

Workup

  1. customThe solvent was removed
  2. customthe residue was chromatographed (50% ethyl acetate/hexanej

Sources & evidence

ORD record
ord-0a2c3cc7dd9d4784831b160000458410
Source dataset
uspto-grants-2009_11
Patent number
US07615634B2

Reaction notes

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