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

HRID 78890Notes

Reaction equation

HRID 78890 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+]>N([C@H]1CCO[C@@H](C(C2C=CC=CC=2)C2C=CC=CC=2)C1)=[N+]=[N-]>[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

4

Reactant 2

HCID 33557Sodium AzideHCID 86605344Methanesulfonic acid cis-2-benzhydryl-tetrahydropyran-4-ylester

Product 1

HCID 86605346trans-4-Azido-2-benzhydryl-tetrahydropyranYield 80.6%

Reagents, catalysts & solvents 1

HCID 86605345cis-4-Azido-2-benzhydryl-tetrahydropyranSolvent

Procedure

Cis-2-diphenylmethylpyran-4-yl methanesulfonate 4b (0.38 g, 1.10 mmol) was reacted with sodium azide (0.29 g, 4.4 mmol) in dry DMF (Procedure B) to yield compound 5b (0.26 g, 80%) as a liquid.

Sources & evidence

ORD record
ord-4d837cfe0243498384dfa67d0e483afa
Source dataset
uspto-grants-2014_09
Patent number
US08841464B2

Reaction notes

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