Hydrochloric Acid → 6-(1-aminoethyl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol hydrochloride

HRID 1037128Notes

Reaction equation

HRID 1037128 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([CH:11]([NH:13]C(=O)OC(C)(C)C)[CH3:12])[CH:9]=[CH:10][C:5]=2[C:4]([CH3:22])([CH3:21])[O:3]1.[ClH:23].O>CO>[ClH:23].[NH2:13][CH:11]([C:8]1[CH:9]=[CH:10][C:5]2[C:4]([CH3:21])([CH3:22])[O:3][B:2]([OH:1])[C:6]=2[CH:7]=1)[CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86685492Tert-butyl 1-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)ethylcarbamate

Product 1

HCID 866854936-(1-aminoethyl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 1-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)ethyl-carbamate (0.93 mmol) in MeOH (10 mL) was added 6N HCl (10 mL). The mixture was stirred at rt overnight. The mixture was poured into water and washed with EA (50 mL×2). The water layer was lyophilized to give crude 6-(1-aminoethyl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol hydrochloride. It was used in the next step without further purification.

Workup

  1. washwashed with EA (50 mL×2)

Sources & evidence

ORD record
ord-ebeb44aa01924eb0a1be282b20d850da
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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