Tetrahydrofuran → 6-[(tert-Butoxycarbonyl)methylamino]-2-pyridylethanol

HRID 1815981노트

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HRID 1815981 반응식
[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]

참가 물질

4

반응물 3

HCID 8028Tetrahydrofuran2회HCID 4148881Lithium borohydrideHCID 22496030Ethyl-6-[(tert-butoxycarbonyl)methylamino]-2-pyridylacetate

생성물 1

HCID 224960276-[(tert-Butoxycarbonyl)methylamino]-2-pyridylethanol수율 88%

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온도
0 °C

실험 절차

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)+.

후처리

  1. temperatureThe reaction was then slowly heated
  2. temperatureto reflux (initial exotherm)
  3. temperatureAfter 16 h at reflux
  4. customcarefully quenched with water (50 mL)
  5. extractionThe mixture was extracted with EtOAc (150 mL)
  6. washthe organic layer was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customPurification by flash chromatography on silica gel (35% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-1f5c5c898b0b4822af143e88c3010568
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06881736B1

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