Sodium borohydride → HCID 57570973, compound

HRID 1695305Notes

Reaction equation

HRID 1695305 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:9]=[C:8]([C:24](OCC)=[O:25])[N:7]=1)=O)C.[BH4-].[Na+].[Cl-].[Ca+2].[Cl-].[H][H]>C(O)C>[C:20]([O:19][C:17]([NH:16][CH2:15][CH2:14][CH2:13][O:12][C:10]1[CH:9]=[C:8]([CH2:24][OH:25])[N:7]=[C:6]([CH2:4][OH:3])[CH:11]=1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 67145385HCID 67145385, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57570973HCID 57570973, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(3-tert-butoxycarbonylamino-propoxy)-pyridine-2,6-dicarboxylic acid diethyl ester (150 mg) in absolute ethanol (5 mL) was added sodium borohydride (43 mg) and calcium chloride (128 mg). After stirring for 4 h, hydrogen evolution ceased, and reaction was quenched with water. Solvent was evaporated under reduced pressure. The residue was then washed into separatory funnel using dichloromethane and water. The layers were separated, and the aqueous layer was extracted three times with dichloromethane. The combined organic solutions were dried over magnesium sulphate, and concentrated in vacuo to give 4-(3-tert-butoxycarbonylamino-propoxy)-2,6-bis-(hydroxymethyl)pyridine (80 mg):

Workup

  1. customreaction
  2. customwas quenched with water
  3. customSolvent was evaporated under reduced pressure
  4. washThe residue was then washed into separatory funnel
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted three times with dichloromethane
  7. dry with materialThe combined organic solutions were dried over magnesium sulphate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9f31a6c0ebfe4bed80ccf0f989f387d4
Source dataset
uspto-grants-2012_04
Patent number
US08163736B2

Reaction notes

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