Triethylamine → HCID 117966463, compound

HRID 931255Notes

Reaction equation

HRID 931255 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C:12]([F:15])([F:14])[CH2:11][CH:10]([C:16]([OH:18])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:19](N1C=CN=C1)([N:21]1C=CN=[CH:22]1)=O.Cl.CNC.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[CH3:19][N:21]([CH3:22])[C:16]([CH:10]1[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:13][C:12]([F:15])([F:14])[CH2:11]1)=[O:18]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 682631,1'-CarbonyldiimidazoleHCID 665217431-(tert-Butoxycarbonyl)-5,5-difluoropiperidine-3-carboxylic acid

Product 1

HCID 117966463HCID 117966463, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)-5,5-difluoropiperidine-3-carboxylic acid (2.1 g, 7.92 mmol) in N,N-dimethylformamide (100 mL) were added 1,1′-carbonyldiimidazole (CDI, 2.56 g, 15.82 mmol), dimethylamine hydrochloride (1.29 g, 15.82 mmol) and triethylamine (2.4 g, 23.71 mmol). After 16 h, the mixture was diluted with ethyl acetate, then was washed sequentially with cold water (×2) and brine, The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography to afford tert-butyl 5-(dimethylcarbamoyl)-3,3-difluoropiperidine-1-carboxylate (1.4 g, 60% over two steps) as a pale yellow solid.

Workup

  1. washwas washed sequentially with cold water (×2) and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5e910dc70f174edd8e157395919c1169
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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