Lithium Chloride → Phenyl 4-(1,3-dihydroxypropan-2-yl)-3-fluorophenylcarbamate

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Reaktionsgleichung

[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:10])[CH:5]=[CH:4][C:3]=1[CH:18]([C:23](OC)=[O:24])[C:19](OC)=[O:20].[BH4-].[Na+].[Cl-].[Li+]>C(O)C.C1COCC1>[OH:24][CH2:23][CH:18]([C:3]1[CH:4]=[CH:5][C:6]([NH:8][C:9](=[O:10])[O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][C:2]=1[F:1])[CH2:19][OH:20]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a stirred solution of dimethyl 2-(2-fluoro-4-(phenoxycarbonylamino)phenyl)malonate (3.0 g, 8.31 mmol, 1.0 eq) in ethanol (15 mL) and THF (15 mL) was added NaBH4 (621 mg, 16.62 mmol, 2.0 eq) followed by lithium chloride (705 g, 16.62 mmol, 2.0 eq) at 0° C. and the mixture was stirred at 0° C. for 5 h. The solvent was evaporated and the residue diluted with water (30 mL) and extracted with EtOAc (2×50 mL). The organic layer was separated, washed with brine, dried over Na2SO4 and evaporated. The residue was purified by CC using MeOH/DCM (1:19) as eluent to get phenyl 4-(1,3-dihydroxypropan-2-yl)-3-fluorophenylcarbamate (482 mg, 19%, white solid; TLC system: MeOH/DCM (1:9), Rf: 0.6)

Aufarbeitung

customThe solvent was evaporated
additionthe residue diluted with water (30 mL)
extractionextracted with EtOAc (2×50 mL)
customThe organic layer was separated
washwashed with brine
dry with materialdried over Na2SO4
customevaporated
customThe residue was purified by CC

Quellen und Nachweise

ORD-Eintrag: ord-2c55536ac0464644b2641751dfe9d37f
Quelldatensatz: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08946204B2

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