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

HRID 495882노트

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HRID 495882 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-58c43f52d21643d69d63c0a7a2892a99
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06942966B1

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