Methanol → 6-(Aminomethyl)-3,3-dimethyl-1,3-dihydro-2,1-benzoxaborol-1-ol

HRID 1037077Notes

Reaction equation

[OH:1][B:2]1[C:6]2[CH:7]=[C:8](/[CH:11]=[N:12]/O)[CH:9]=[CH:10][C:5]=2[C:4]([CH3:15])([CH3:14])[O:3]1.CO>CC(O)=O.[Zn]>[NH2:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]2[C:4]([CH3:15])([CH3:14])[O:3][B:2]([OH:1])[C:6]=2[CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of crude compound (E)-1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbaldehyde oxime (47.4 mmol) in AcOH (60 mL) at rt was added zinc dust (12.3 g, 190 mmol). The reaction mixture was stirred at 40° C. for 4 h under argon atmosphere. Methanol was added and the mixture was filtered over Celite. The filtrate was concentrated and dissolved in ethyl acetate. The organic layer was washed with water. The water layer was lyophilized to give the crude compound 6-(aminomethyl)-3,3-dimethylbenzo[c][1,2]oxaborol-1(3H)-ol as a light yellow solid. It was used in next step without further purification. MS: m/z=192.0 (M+1, ESI+).

Workup

filtrationthe mixture was filtered over Celite
concentrationThe filtrate was concentrated
dissolutiondissolved in ethyl acetate
washThe organic layer was washed with water

Sources & evidence

ORD record: ord-f9573d0cfe894ce1b5563f4021313743
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546357B2

Reaction notes

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