Potassium Carbonate → Methyl 5-(4-ethylphenyl)-1-[(3-hydroxyazetidin-1-yl)carbonyl]piperidine-3-carboxylate

HRID 661203Notes

Reaction equation

HRID 661203 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][N:13]([C:15]([O:17]C3C=CC([N+]([O-])=O)=CC=3)=O)[CH2:12][CH:11]([C:27]([O:29][CH3:30])=[O:28])[CH2:10]2)=[CH:5][CH:4]=1)[CH3:2].Cl.[OH:32][CH:33]1[CH2:36][NH:35][CH2:34]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:14][N:13]([C:15]([N:35]3[CH2:36][CH:33]([OH:32])[CH2:34]3)=[O:17])[CH2:12][CH:11]([C:27]([O:29][CH3:30])=[O:28])[CH2:10]2)=[CH:7][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27592903-Hydroxyazetidine hydrochlorideHCID 580023823-Methyl 1-(4-nitrophenyl) 5-(4-ethylphenyl)piperidine-1,3-dicarboxylate

Product 1

HCID 58002725Methyl 5-(4-ethylphenyl)-1-[(3-hydroxyazetidin-1-yl)carbonyl]piperidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.3 g (0.7 mmol) of the compound from Example 12A, 0.2 g (2.18 mmol) of 3-hydroxyazetidine hydrochloride and 0.2 g (1.4 mmol) of potassium carbonate were initially charged in 6 ml of DMF and reacted in a single-mode microwave (Emrys Optimizer) at 150° C. for 30 min. The crude product was purified by preparative HPLC. Yield: 105 mg (40% of theory)

Workup

  1. customreacted in a single-mode microwave (Emrys Optimizer) at 150° C. for 30 min
  2. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-633ff45931a149b9a4bd463a1e4b9718
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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