Ethyl Acetate → HCID 45786893, compound

HRID 1512105Notes

Reaction equation

HRID 1512105 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].Cl[C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][N:27]=1.CCOC(C)=O>CN(C=O)C.O>[N+:32]([C:29]1[CH:30]=[CH:31][C:26]([O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)=[N:27][CH:28]=1)([O-:34])=[O:33]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 783082-Chloro-5-nitropyridineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 45786893HCID 45786893, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (1 eq) in DMF was added potassium bis-trimethylsilylamide (1.5 eq, 1M solution in tetrahydrofuran). The solution was stirred at room temperature for 10 minutes, and 2-chloro-5-nitropyridine (1.2 eq) was added. The reaction mixture was submitted to microwave irradiation for 600 seconds at 145° C. EtOAc and water were added to the reaction and the layers separated. The organic layer was washed with water, brine, dried over sodium sulfate and evaporated to give brown crude material. Purification by silica gel column chromatography using 10% EtOAc/hexane afforded the product as a light yellow solid. LC/MS (m/z): 324.3 (MH+) Rt 3.33 minutes

Workup

  1. customirradiation for 600 seconds at 145° C
  2. customthe layers separated
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customto give brown crude material
  7. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-f9ccd7948fcc4e838c61eafb84aaf189
Source dataset
uspto-grants-2012_07
Patent number
US08217035B2

Reaction notes

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