Sodium borohydride → HCID 59615963, compound

HRID 1950753Notes

Reaction equation

HRID 1950753 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:9]=[C:8]([C:31](OCC)=[O:32])[N:7]=1)=O)C.[BH4-].[Na+].[Cl-].[Ca+2].[Cl-].[H][H]>C(O)C>[C:27]([O:26][C:24](=[O:25])[CH2:23][CH2:22][O:21][CH2:20][CH2:19][O:18][CH2:17][CH2:16][O:15][CH2:14][CH2:13][O:12][C:10]1[CH:11]=[C:6]([CH2:4][OH:3])[N:7]=[C:8]([CH2:31][OH:32])[CH:9]=1)([CH3:30])([CH3:28])[CH3:29]

Participants

6

Reactant 4

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 59615973HCID 59615973, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59615963HCID 59615963, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(2-{2-[2-(2-tert-Butoxycarbonyl-ethoxy)-ethoxy]-ethoxy}-ethoxy)-pyridine-2,6-dicarboxylic acid diethyl ester (1.36 g) in absolute ethanol (72 mL) was added sodium borohydride (309 mg) and calcium chloride (921 mg). After stirring for 30 mn, hydrogen evolution ceased, and reaction was quenched with water. After concentration under reduced pressure, ammonium chloride was added and the aqueous phase was extracted three times with ethyl acetate. The combined organic solutions were dried over magnesium sulfate, and concentrated in vacuo to a residue. The residue was purified by silica gel chromatography (Analogix Super Flash SiO2 SF25-80 g), using gradient elution with a mixture of DCM (A) and MeOH (B) (gradient: 100% A down to 90% A: 10% B) to give 3-(2-{2-[2-(2,6-Bis-hydroxymethyl-pyridin-4-yloxy)-ethoxy]-ethoxy}-ethoxy)-propionic acid tert-butyl ester (720 mg): LC/MS (Method A3): ES: m/z 416 (M+H)+; RT=0.52 min

Workup

  1. customreaction
  2. customwas quenched with water
  3. concentrationAfter concentration under reduced pressure, ammonium chloride
  4. additionwas added
  5. extractionthe aqueous phase was extracted three times with ethyl acetate
  6. dry with materialThe combined organic solutions were dried over magnesium sulfate
  7. concentrationconcentrated in vacuo to a residue
  8. customThe residue was purified by silica gel chromatography (Analogix Super Flash SiO2 SF25-80 g)
  9. washelution
  10. additionwith a mixture of DCM (A) and MeOH (B) (gradient

Sources & evidence

ORD record
ord-b418e6f1b3b647408401d35a3ec56d79
Source dataset
uspto-grants-2013_03
Patent number
US08404678B2

Reaction notes

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