Hydrochloric Acid → HCID 86685457, compound

HRID 1037014Notes

Reaction equation

HRID 1037014 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[C:4]([CH3:21])([CH3:20])[O:3]1.[ClH:22]>CO>[ClH:22].[NH2:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]2[C:4]([CH3:21])([CH3:20])[O:3][B:2]([OH:1])[C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86685463Tert-butyl (1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)methylcarbamate

Product 1

HCID 86685457HCID 86685457, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl ((1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)methyl)carbamate (13.15 mmol) in methanol (100 mL) was added HCl (20 mL, 65.75 mmol). The reaction mixture was stirred for 16 h at rt. The solvent was removed to give 6-(aminomethyl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol hydrochloride (1.5 g; yield 50% over 4 steps). MS: m/z=192.1 (M+1, ESI+).

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-a524bed128174156af3e72fbc70164d7
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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