Sodium Azide → HCID 86659973, compound

HRID 72333Notes

Reaction equation

HRID 72333 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([CH2:20]Cl)[O:17][N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:22]=[N+:23]=[N-:24].[Na+]>CN(C=O)C>[N:22]([CH2:20][C:18]1[O:17][N:16]=[C:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:10][CH:11]=2)[CH:19]=1)=[N+:23]=[N-:24]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 574983013-(4-Benzyloxy-phenyl)-5-chloromethyl-isoxazole

Product 1

HCID 86659973HCID 86659973, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.13 g of 3-(4-benzyloxy-phenyl)-5-chloromethyl-isoxazole was dissolved in 10 ml of DMF, to which solution was added 85 mg (3 equivalents) of NaN3, and the mixture was stirred for 12 hours. The solvent was dried off under reduced pressure and removed, followed by column chromatography to obtain 5-azidomethyl-3-(4-benzyloxy-phenyl)-isoxazole. A reduction of the compound was performed under NaBH4 conditions to obtain C-[3-(4-benzyloxy-phenyl)-isoxazol-5-yl]-methylamine as a desired compound.

Workup

  1. customThe solvent was dried off under reduced pressure
  2. customremoved

Sources & evidence

ORD record
ord-b451e2afa2ac4eec9be56af186b0a9e0
Source dataset
uspto-grants-2014_09
Patent number
US08828992B2

Reaction notes

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