Sodium borohydride → 4-(3-Azidopropoxy)-2,6-dihydroxymethylpyridine

HRID 495882ノート

反応式

HRID 495882 の反応式
C([O:3][C:4]([C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][CH2:15][N:16]=[N+:17]=[N-:18])[CH:9]=[C:8]([C:19](OCC)=[O:20])[N:7]=1)=O)C.[BH4-].[Na+].[Cl-].[Cl-].[Ca+2].[H][H]>ClCCl.C(O)C.O>[N:16]([CH2:15][CH2:14][CH2:13][O:12][C:10]1[CH:11]=[C:6]([CH2:4][OH:3])[N:7]=[C:8]([CH2:19][OH:20])[CH:9]=1)=[N+:17]=[N-:18]

参加物

8

反応物 4

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 22323654Diethyl-4-(3-azidopropoxy)-2,6-pyridinedicarboxylateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 543426824-(3-Azidopropoxy)-2,6-dihydroxymethylpyridine

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of Diethyl-4-(3-azidopropoxy)-2,6-pyridinedicarboxylate (4.2 mmol) in dichloromethane (10 mL) and absolute ethanol (15 mL), was added in portions, NaBH4 (4.2 mmol) at 25° C. Powdered CaCl2 (4.2 mmol) was added cautiously in small portions and the evolution of hydrogen was allowed to cease before each further addition. The reaction mixture was stirred for 2 hours. Water (100 mL) was added and the reaction mixture was extracted several times with ethyl acetate. The ethyl acetate layers were combined, dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by silica gel flash column chromatography to give the title compound. 1H NMR (DMSO) δ 2.00 (m, 2H, CH2), 3.52 (t, 2H, CH2), 4.13 (t, 2H, CH2), 4.45 (d, 4H, 2x CH2), 5.36 (t, 2H, 2x OH), 6.87 (s, 2H, 2x AR).

後処理

  1. additionto cease before each further addition
  2. extractionthe reaction mixture was extracted several times with ethyl acetate
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified by silica gel flash column chromatography

出典と根拠

ORDレコード
ord-58c43f52d21643d69d63c0a7a2892a99
出典データセット
uspto-grants-2005_09
特許番号
US06942966B1

反応ノート

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