2-Fluoropyridine → 1-Boc-4-(2-pyridyloxy)piperidine

HRID 555785Notes

Reaction equation

HRID 555785 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].F[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1.[H-].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 97462-FluoropyridineHCID 24758Sodium hydrideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 219060391-Boc-4-(2-pyridyloxy)piperidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of tert-Butyl-4-hydroxy-1-piperidine-carboxylate (2.0 g, 9.64 mmol) and 2-Fluoropyridine (0.93 mL, 10.6 mmol) in DMF (10 mL) is treated with 60% NaH in mineral oil (600 mg, 12.5 mmol) at RT. After completion, the reaction mixture is quenched by H2O, EtOAc is added and the organic layer is washed with brine, dried over MgSO4 and evaporated in vacuo. Silica gel flash chromatography of the residue affords the title compound as a white powder; ES-MS: M+H=279.0: DtRet=2.82.

Workup

  1. customAfter completion, the reaction mixture is quenched by H2O, EtOAc
  2. additionis added
  3. washthe organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-301847f46a4748e4ab8bfe2f06fc6d64
Source dataset
uspto-grants-2011_11
Patent number
US08053457B2

Reaction notes

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