Sodium borohydride → tert-Butyl 2-(hydroxymethyl)-6-phenylpyridin-3-ylcarbamate

HRID 2249501Notizen

Reaktionsgleichung

[CH:1]([C:3]1[C:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:7][CH:6]=[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:4]=1)=[O:2].[BH4-].[Na+]>C1COCC1.C(O)C>[OH:2][CH2:1][C:3]1[C:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:7][CH:6]=[C:5]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:4]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of 1E (2.37 g, 7.94 mmol) in THF (10 mL) and ethanol (20 mL) at 0° C. was added sodium borohydride (300 mg, 7.94 mmol) in several portions. After addition, the reaction was stirred at 0° C. for 10 min, and no starting material was detected by LC-MS. The resultant mixture was quenched with saturated aqueous NaHCO3 (30 mL) and extracted with EtOAc (3×30 mL). The combined organic layers were washed with saturated NaCl, dried (Na2SO4), filtered and concentrated. The resulting residue was purified by silica gel (120 g) column chromatography eluting with a isocratic of 15% EtOAc in hexane to give the title compound as a white solid (2.25 g, 95%). LC/MS (method A): retention time=3.06 min, (M+H)+=301.

Aufarbeitung

additionAfter addition
customThe resultant mixture was quenched with saturated aqueous NaHCO3 (30 mL)
extractionextracted with EtOAc (3×30 mL)
washThe combined organic layers were washed with saturated NaCl
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe resulting residue was purified by silica gel (120 g) column chromatography
washeluting with a isocratic of 15% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag: ord-4fd2cefd348e4477bb20532a116e9c31
Quelldatensatz: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07314882B2

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