Triisopropyl borate → HCID 68106333, compound

HRID 2403586Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([O:18][B:19](OC(C)C)[O:20]C(C)C)(C)C.C([Li])CCC.CCCCCC.[Cl-].[NH4+]>C1COCC1>[N:8]1([C:5]2[CH:6]=[CH:7][C:2]([B:19]([OH:20])[OH:18])=[CH:3][CH:4]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

Conditions

Temperature: -78 °C

Procedure

Under an argon atmosphere, 1-(4-iodophenyl)azepane (200 mg) and triisopropylborate (162 mg) were dissolved in THF (2 ml), followed by cooling to −78° C. A 1.59 M butyl lithium/hexane solution (0.5 ml) was added thereto, followed by elevating the temperature to 0° C. over 1 hour, and further stirring at the same temperature for 1 hour. To the reaction mixture was added a saturated aqueous ammonium chloride solution, followed by extraction with EtOAc. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH) to obtain (4-azepan-1-ylphenyl)boronic acid (52 mg).

Workup

customto 0° C.
customover 1 hour
extractionfollowed by extraction with EtOAc
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record: ord-dd3e42c327ab4e47880525ff27b45d3d
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802679B2

Reaction notes

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