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

HRID 2269684Notes

Reaction equation

HRID 2269684 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 (MgSO4) and concentrated in vacuo. The resultant residue was purified by silica gel flash column chromatography to give the title compound. 1H NMR (DMSO) δ2.00 (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).

Workup

  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

Sources & evidence

ORD record
ord-4f3c34c258dd471aa018f786318dc7d9
Source dataset
uspto-grants-2001_12
Patent number
US06329523B1

Reaction notes

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