Borane;tetrahydrofuran → (7RS)-7-(3,4-dichlorophenyl)-7-(methoxymethyl)-1,4-oxazepane monohydrochloride

HRID 1022582Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:17][O:18][CH3:19])[O:15][CH2:14][C:13](=O)[NH:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].B.C1COCC1>C1COCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:17][O:18][CH3:19])[O:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of (7RS)-7-(3,4-dichlorophenyl)-7-(methoxymethyl)-1,4-oxazepan-3-one (535 mg) in THF (10 ml) was added 1 M borane-THF solution (5 ml), and the mixture was stirred at 70° C. for 30 min. The reaction mixture was quenched with water, 2N hydrochloric acid (5 mL) was added, and the mixture was stirred at 70° C. for 10 min. The solvent was evaporated under reduced pressure, the residue was alkalified with potassium hydroxide, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (NH, eluent; hexane:ethyl acetate (1:1)-(0:10)) to give the title compound as a free amine form (397 mg).

Workup

customThe reaction mixture was quenched with water, 2N hydrochloric acid (5 mL)
additionwas added
stirringthe mixture was stirred at 70° C. for 10 min
customThe solvent was evaporated under reduced pressure
extractionthe mixture was extracted three times with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated
customThe residue was purified by silica gel column chromatography (NH, eluent; hexane:ethyl acetate (1:1)-(0:10))

Sources & evidence

ORD record: ord-dcf14bf988ba4c3699ac33b8b19109fc
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722662B2

Reaction notes

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