Borane;tetrahydrofuran → HCID 57588493, compound

HRID 1782192Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[CH:13]=[C:12]([C:14]2[CH:15]=[C:16]([NH:20][C:21](=O)[CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:17]=[CH:18][CH:19]=2)[O:11][N:10]=1.B.O1CCCC1>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[CH:13]=[C:12]([C:14]2[CH:15]=[C:16]([NH:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[CH:17]=[CH:18][CH:19]=2)[O:11][N:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

tert-Butyl 2-(3-(3-(2,6-dichlorophenyl)isoxazol-5-yl)phenylamino)-2-oxoethylcarbamate (500 mg, 1.08 mmol) was dissolved in anhydrous tetrahydrofuran (10 mL) and cooled to 0° C. Borane-tetrahydrofuran complex (1M soln in THF, 10.8 mL, 10.8 mmol) was added dropwise to the cool solution. The reaction mixture was allowed to stir while slowly warming to room temperature for 5 h. The reaction was quenched with 1N hydrochloric acid (25 mL) and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure to yield tert-butyl 2-(3-(3-(2,6-dichlorophenyl)isoxazol-5-yl)phenylamino)ethylcarbamate as a white solid. The product was carried forward without further purification. 1H NMR (CDCl3): 7.98 (s, 1H), 7.55-7.50 (m, 2H), 7.48-7.35 (m, 4H), 6.48 (s, 1H), 5.18 (br s, 1H), 4.00 (m, 2H), 3.58 (m, 2H), 1.48 ppm (s, 9H).

Workup

temperaturewhile slowly warming to room temperature for 5 h
customThe reaction was quenched with 1N hydrochloric acid (25 mL)
extractionextracted with ethyl acetate
concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record: ord-43f83f8c6bec4f0fa47db2bdd986dc0c
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07498353B2

Reaction notes

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