Tetrahydrofuran → 6-[(tert-Butoxycarbonyl)methylamino]-2-pyridylethanol
Reaction equation
[Li+].[BH4-].C(O[C:6](=O)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[N:9]=1)C.C1C[O:27]CC1>>[C:19]([O:18][C:16]([CH2:15][NH:14][C:10]1[N:9]=[C:8]([CH:7]([OH:27])[CH3:6])[CH:13]=[CH:12][CH:11]=1)=[O:17])([CH3:22])([CH3:21])[CH3:20]Participants
Conditions
- Temperature
- 0 °C
Procedure
A solution of 2 N LiBH4 in THF (7 mL, 14 mmole) was added via syringe to a stirred solution of ethyl-6-[(tert-butoxycarbonyl)methylamino]-2-pyridylacetate (6.97 g, 23.7 mmole) in anhydrous THF (30 mL) under argon. The reaction was then slowly heated to reflux (initial exotherm). After 16 h at reflux, the reaction was cooled to 0° C. and carefully quenched with water (50 mL). The mixture was extracted with EtOAc (150 mL), and the organic layer was washed with brine, dried (Na2SO4), and concentrated. Purification by flash chromatography on silica gel (35% EtOAc/hexane) gave the title compound (5.26 g, 88%) as a clear oil: 1H NMR (400 MHz, CDCl3) δ 7.57 (m, 2H), 6.88 (d, J=7.2 Hz, 1H), 4.01 (t, 2H), 3.39 (s, 3H), 3.00 (t, 2H), 1.53 (s, 9H); MS (ES) m/e 253.2 (M+H)+.
Workup
- temperatureThe reaction was then slowly heated
- temperatureto reflux (initial exotherm)
- temperatureAfter 16 h at reflux
- customcarefully quenched with water (50 mL)
- extractionThe mixture was extracted with EtOAc (150 mL)
- washthe organic layer was washed with brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customPurification by flash chromatography on silica gel (35% EtOAc/hexane)
Sources & evidence
- ORD record
- ord-1f5c5c898b0b4822af143e88c3010568
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06881736B1
Reaction notes
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