Dimethylformamide → HCID 69055376, compound

HRID 1727221Notes

Reaction equation

HRID 1727221 reaction equation
[H-].[Na+].CN(C)C=O.[OH:8][CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]1.[F:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][C:30]=1[F:31])[CH2:26]Br>CCCCC>[F:22][C:23]1[CH:24]=[C:25]([CH2:26][O:8][CH:9]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]2)[CH:28]=[CH:29][C:30]=1[F:31]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 5456991-Boc-3-hydroxypiperidineHCID 5814364-(Bromomethyl)-1,2-difluorobenzene

Product 1

HCID 69055376HCID 69055376, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

To sodium hydride (60% w/w dispersion in oil, 0.62 g, 16.4 mmol) washed in pentane was added N,N-dimethylformamide (20 ml) and then 1,1-dimethylethyl 3-hydroxypiperidine-1-carboxylate (Preparation 117, 3.0 g, 14.9 mmol). The reaction mixture was stirred for 1 h, before adding 3,4-difluorobenzyl bromide (2.0 ml, 16.4 mmol) and stirring the reaction mixture for 18 h. The reaction mixture was concentrated in vacuo and the crude residue was dissolved in dichloromethane and washed with brine and dried (MgSO4) before concentrating in vacuo. The crude residue was purified by flash chromatography to give the title compound (4.58 g, 94%).

Workup

  1. stirringstirring the reaction mixture for 18 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe crude residue was dissolved in dichloromethane
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationbefore concentrating in vacuo
  7. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-b11729271d4243d9840bb77d6af73ac2
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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