Triethylamine → HCID 43652195, compound

HRID 1618108Notes

Reaction equation

HRID 1618108 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=O)[CH3:7].[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([NH2:22])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(N(CC)CC)C.C([BH3-])#N.[Na+].[OH-].[Na+]>ClCCl.CO>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([NH:22][CH:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[CH3:7])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 145052-AcetylfuranHCID 14798Sodium HydroxideHCID 12682914-Amino-1-Boc-piperidineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 43652195HCID 43652195, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To an equimolar solution of 1-furan-2-yl-ethanone (250 mg, 2.27 mmol) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester (454 mg, 2.27 mmol) in dichloromethane (14 mL) 1M titanium(IV) chloride in dichloromethane (1.13 mL, 1.13 mmol) and triethylamine (0.31 mL, 2.27 mmol) were added. The reaction mixture was stirred under nitrogen atmosphere for 2 days. Then sodium cyanoborohydride (430 mg, 6.8 mmol) in methanol (7 mL) was added dropwise with stirring and the solution was allowed to stir overnight at room temperature. 35% sodium hydroxide was added and the product was extracted with ethyl acetate. The solvent was removed under reduce pressure and the crude was purified by flash chromatography (dichloromethane/methanol:95/5) to give the final compound as a red oil (406 mg, 61%).

Workup

  1. stirringwith stirring
  2. stirringto stir overnight at room temperature
  3. extractionthe product was extracted with ethyl acetate
  4. customThe solvent was removed
  5. customthe crude was purified by flash chromatography (dichloromethane/methanol:95/5)

Sources & evidence

ORD record
ord-87b9f90e32de41ff8c1366c62e4d3576
Source dataset
uspto-grants-2014_07
Patent number
US08765972B2

Reaction notes

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