tert-Butyl (1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)methylcarbamate → 6-(aminomethyl)benzo[c][1,2]oxaborol-1(3H)-ol

HRID 1425937Notes

Reaction equation

HRID 1425937 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([CH2:11][NH:12]C(=O)OC(C)(C)C)[CH:9]=[CH:10][C:5]=2[CH2:4][O:3]1>Cl.CCOC(C)=O>[NH2:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]2[CH2:4][O:3][B:2]([OH:1])[C:6]=2[CH:7]=1

Participants

3

Reactant 1

HCID 86702804tert-Butyl (1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)methylcarbamate

Product 1

HCID 682815336-(aminomethyl)benzo[c][1,2]oxaborol-1(3H)-olYield 74%

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

tert-Butyl (1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)methylcarbamate (CXI) (0.27 g, 1.02 mmol) was dissolved in HCl/EtOAc (4.2 M, 7 mL/mmol) and stirred for 30 minutes at room temperature. The solvent was removed under vacuum and residue was triturated with Et2O to give 6-(aminomethyl)benzo[c][1,2]oxaborol-1(3H)-ol (CXII) as a white solid (0.15 g, 0.75 mmol, 74% yield). 1H NMR (DMSO-d6) δ ppm 4.00 (s, 2H), 4.69 (s, 2H), 7.21-7.51 (brs, 1H), 7.52-7.66 (brs, 1H), 7.67-7.88 (brs, 1H), 8.06-8.98 (brs, 3H); ESIMS found for C8H10BNO2 m/z 146.7 (M−H2O+1).

Workup

  1. customThe solvent was removed under vacuum and residue
  2. customwas triturated with Et2O

Sources & evidence

ORD record
ord-e6d4b1dc415a46a3a0f1e11ab6ce4b51
Source dataset
uspto-grants-2015_01
Patent number
US08933018B2

Reaction notes

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