Methanol → HCID 68005967, compound

HRID 1026602Notes

Reaction equation

HRID 1026602 reaction equation
CO.[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([N:16]2[C:25]3[C:20](=[N:21][CH:22]=[C:23]([Cl:26])[CH:24]=3)[CH2:19][C:18]([CH3:32])([C:27](OCC)=[O:28])[C:17]2=[O:33])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[Cl-].[Ca+2].[Cl-].[BH4-].[Na+]>O>[Cl:26][C:23]1[CH:24]=[C:25]2[C:20]([CH2:19][C:18]([CH2:27][OH:28])([CH3:32])[C:17](=[O:33])[N:16]2[CH:13]2[CH2:14][CH2:15][N:10]([C:8]([O:7][C:3]([CH3:4])([CH3:5])[CH3:6])=[O:9])[CH2:11][CH2:12]2)=[N:21][CH:22]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 68006317HCID 68006317, compound

Product 1

HCID 68005967HCID 68005967, compoundYield 20.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a methanol solution (4 ml) of ethyl 1-[1-(tert-butoxycarbonyl)piperidin-4-yl]-7-chloro-3-methyl-2-oxo-1,2,3,4-tetrahydro-1,5-naphthyridine-3-carboxylate (163 mg) was added at 0° C. calcium chloride (162 mg), followed by stirring for 15 minutes. Then, sodium borohydride (115 mg) was added, and stirred for 2 hours. Water was added to the reaction solution, and extracted with ethyl acetate. The collected organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel thin layer chromatography to afford tert-butyl 4-[7-chloro-3-(hydroxymethyl)-3-methyl-2-oxo-3,4-dihydro-1,5-naphthyridin-1(2H)-yl]piperidine-1-carboxylate (30.8 mg).

Workup

  1. stirringstirred for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe collected organic layer was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel thin layer chromatography

Sources & evidence

ORD record
ord-579fb26ff15a4d7aa96317c9149bc9a9
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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