1-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine → HCID 58424890, compound

HRID 2409408Notes

Reaction equation

HRID 2409408 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]2[NH:6][C:7](=[O:15])[C:8]3[CH2:9][CH2:10][CH2:11][N:12]([CH3:14])[C:13]=3[C:4]=2[CH:3]=1.CS(O[CH:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]1)(=O)=O>C(#N)C.CN(C)C=O>[CH3:14][N:12]1[C:13]2[C:4]3[CH:3]=[C:2]([O:1][CH:23]4[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]4)[CH:17]=[CH:16][C:5]=3[NH:6][C:7](=[O:15])[C:8]=2[CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 58424854HCID 58424854, compound

Product 1

HCID 58424890HCID 58424890, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

9-Hydroxy-1-methyl-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridine-5(6H)-one (60 mg, 0.26 mmol) prepared at Example 10 was dissolved in acetonitrile (8 ml)/N,N-dimethylformamide (4 ml), added with t-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (220 mg, 0.78 mmol) at room temperature. The resulting mixture was stirred for four days at 90˜100° C. and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure. The residue was then purified with flash column chromatography (chloroform:methanol=20:1) to obtain the title compound (70 mg, yield: 65%, brown oil).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was then purified with flash column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-09baa9b46b73480c84dd3c1673259775
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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