Water → HCID 67426414, compound

HRID 2264354Notes

Reaction equation

HRID 2264354 reaction equation
CC(C)([O-])C.[K+].[OH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1.F[C:22]1[CH:23]=[CH:24][C:25]([N+:28]([O-:30])=[O:29])=[N:26][CH:27]=1.O>CC(N(C)C)=O>[C:17]([O:16][C:14]([N:11]1[CH2:10][CH2:9][CH:8]([O:7][C:22]2[CH:27]=[N:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)[CH2:13][CH2:12]1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 167481095-Fluoro-2-nitropyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 67426414HCID 67426414, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

Add potassium tert-butoxide (4.84 g) to a solution of tert-butyl 4-hydroxy-1-piperidine-carboxylate (8.76 g) in dimethylacetamide (DMA, 39 mL) at 0° C. under nitrogen. Stir for 1 h and add drop wise a solution 5-fluoro-2-nitro-pyridine (5 g) in DMA (78 mL). Let the reaction stir at RT overnight. Add water and stand for 1 h. Filter, wash with water. Purify by silica gel column chromatography eluting with DCM/EA (0-15%) to afford 5.65 g of the title compound. MS (ES+): m/z=324 (M+H)+.

Workup

  1. stirringstir at RT overnight
  2. filtrationFilter
  3. washwash with water
  4. customPurify by silica gel column chromatography
  5. washeluting with DCM/EA (0-15%)

Sources & evidence

ORD record
ord-e1bacd6cf4e64e4e87803710fa8575fe
Source dataset
uspto-grants-2010_12
Patent number
US07855211B2

Reaction notes

Loading…