Sodium Azide → cis-4-Azido-2-benzhydryl-tetrahydropyran

HRID 1897873Notes

Reaction equation

HRID 1897873 reaction equation
[CH:1]([C@H:14]1[CH2:19][C@H:18](OS(C)(=O)=O)[CH2:17][CH2:16][O:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C=O)C.C(OCC)C>[N:25]([C@H:18]1[CH2:17][CH2:16][O:15][C@@H:14]([CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:19]1)=[N+:26]=[N-:27]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86605343methanesulfonic acid Trans-2-benzhydryl-tetrahydropyran-4-yl ester

Product 1

HCID 86605345cis-4-Azido-2-benzhydryl-tetrahydropyranYield 82.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Into a solution of trans-2-diphenylmethylpyran-4-yl methanesulfonate 4a (0.33 g, 0.95 mmol) in dry DMF (40 ml) was added sodium azide (0.18 g, 2.85 mmol). The mixture was heated to 100° C. and stirred for 4 hr. The mixture was diluted with ethyl ether, washed with 2M aqueous NaHCO3 and brine, and then dried over anhydrous Na2SO4. Removal of the solvent and purification by flash chromatography (Hexane/Ethyl Acetate 9:1) afforded compound 5a (0.23 g, 82.7% yield) as a liquid.

Workup

  1. washwashed with 2M aqueous NaHCO3 and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. customRemoval of the solvent and purification by flash chromatography (Hexane/Ethyl Acetate 9:1)

Sources & evidence

ORD record
ord-040c8d8e7b9b4fc59f915424e98ccb8e
Source dataset
uspto-grants-2013_08
Patent number
US08519159B2

Reaction notes

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