6-(2-azidopropan-2-yl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol → 6-(2-aminopropan-2-yl)-3,3-dimethylbenzo[c][1,2]-oxaborol-1(3H)-ol

HRID 1037052Notes

Reaction equation

HRID 1037052 reaction equation
[N:1]([C:4]([C:7]1[CH:8]=[CH:9][C:10]2[C:14]([CH3:16])([CH3:15])[O:13][B:12]([OH:17])[C:11]=2[CH:18]=1)([CH3:6])[CH3:5])=[N+]=[N-]>CO>[NH2:1][C:4]([C:7]1[CH:8]=[CH:9][C:10]2[C:14]([CH3:16])([CH3:15])[O:13][B:12]([OH:17])[C:11]=2[CH:18]=1)([CH3:6])[CH3:5]

Participants

3

Reactant 1

HCID 866854956-(2-azidopropan-2-yl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol

Product 1

HCID 866854976-(2-aminopropan-2-yl)-3,3-dimethylbenzo[c][1,2]-oxaborol-1(3H)-olYield 111.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The solution of 6-(2-azidopropan-2-yl)-3,3-dimethylbenzo[c][1,2]-oxaborol-1(3H)-ol (100 mg) in MeOH (6 mL) was hydrogenated under H2 using 10% Pd/C (15 mg) as catalyst at atmospheric pressure for 5 h. The catalyst was removed by filtration, and the solvent was evaporated at reduced pressure to give crude product 6-(2-aminopropan-2-yl)-3,3-dimethylbenzo[c][1,2]oxa-borol-1(3H)-ol (100 mg) as colorless oil. It was used without further purification in the next step.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated at reduced pressure

Sources & evidence

ORD record
ord-dfceee58e2474690adac0c3d68721a9c
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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