Furfural → 1-N-Boc-4-(2-furfurylmethylamino)piperidine

HRID 333210Notes

Reaction equation

HRID 333210 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([NH2:21])[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].C(N(CC)CC)C.C([BH3-])#N.[Na+].[OH-].[Na+]>ClCCl.CO>[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([NH:21][CH2:6][C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

8

Reactant 5

HCID 7362FurfuralHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 12682914-Amino-1-Boc-piperidineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 27610481-N-Boc-4-(2-furfurylmethylamino)piperidineYield 56%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To an equimolar solution of furan-2-carbaldehyde (250 mg, 2.6 mmol) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester (473 mg, 2.6 mmol) in dichloromethane (14 mL) 1M titanium(IV) chloride in dichloromethane (1.3 mL, 1.3 mmol) and triethylamine (0.32 mL, 2.6 mmol) were added. The reaction mixture was stirred under nitrogen atmosphere for 2 days. Then sodium cyanoborohydride (493 mg, 7.8 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 title compound as a red oil (406 mg, 56%).

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-6f5acd451d434a5a9644ab83292f7413
Source dataset
uspto-grants-2014_11
Patent number
US08877944B2

Reaction notes

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