Triethylamine → HCID 28167727, compound

HRID 931120Notes

Reaction equation

HRID 931120 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14]([OH:16])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17](N1C=CN=C1)([N:19]1C=CN=[CH:20]1)=O.C(N(CC)CC)C.Cl.CNC>CN(C)C=O>[CH3:17][N:19]([CH3:20])[C:14]([C@@H:10]1[CH2:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1)=[O:16]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 682631,1'-CarbonyldiimidazoleHCID 6435161-(1,1-Dimethylethyl) (3R)-1,3-piperidinedicarboxylate

Product 1

HCID 28167727HCID 28167727, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (R)-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid (10 g, 43.6 mmol) in N,N-dimethylformamide (150 mL) was added 1,1′-carbonyldiimidazole (14.13 g, 87.23 mmol). The reaction mixture was stirred at room temperature for 10 min. Triethylamine (18.3 mL, 130.2 mmol) and dimethylamine hydrochloride (7.1 g, 87.2 mmol) were then added sequentially. The reaction mixture was stirred at room temperature for 16 h. The solvent was evaporated and the residue was treated with cold water and was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified via flash chromatography to afford (R)-tert-butyl 3-(dimethylcarbamoyl)piperidine-1-carboxylate (0.9 g, 80%). MS (ES+APCI) (M+H) 257.1; LCMS retention time: 2.829 min (Method D1)

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 16 h
  2. customThe solvent was evaporated
  3. additionthe residue was treated with cold water
  4. extractionwas extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified via flash chromatography

Sources & evidence

ORD record
ord-a7828466c8f349f1911b0f3da4e96a8b
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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