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

HRID 392022Notes

Reaction equation

HRID 392022 reaction equation
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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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 (MgSO4and 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, 2×CH2), 5.36 (t, 2H, 2×OH), 6.87 (s, 2H, 2×AR

Workup

  1. additionto cease before each further addition
  2. extractionthe reaction mixture was extracted several times with ethyl acetate
  3. dry with materialThe ethyl acetate layers were combined dried (MgSO4and
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-3912e7dd11f3490bbde81b1d4dac940f
Source dataset
uspto-grants-2004_10
Patent number
US06800444B1

Reaction notes

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