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

HRID 1815981ノート

反応式

HRID 1815981 の反応式
[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]

参加物

4

反応物 3

HCID 8028Tetrahydrofuran2 回HCID 4148881Lithium borohydrideHCID 22496030Ethyl-6-[(tert-butoxycarbonyl)methylamino]-2-pyridylacetate

生成物 1

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

反応条件

温度
0 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-1f5c5c898b0b4822af143e88c3010568
出典データセット
uspto-grants-2005_04
特許番号
US06881736B1

反応ノート

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