Furfural → HCID 22018852, compound

HRID 351166Notes

Reaction equation

HRID 351166 reaction equation
C(OC([N:8]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][CH:18]2[C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH2:21][CH2:20][CH2:19]2)=[CH:12][CH:11]=1)=O)(C)(C)C.[CH:35](=O)[C:36]1[O:40][CH:39]=[CH:38][CH:37]=1.[BH3-]C#N.[Na+]>CO>[N:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[CH2:28][NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]([CH2:35][C:36]2[O:40][CH:39]=[CH:38][CH:37]=2)[CH:18]2[C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH2:21][CH2:20][CH2:19]2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7362FurfuralHCID 5003444Sodium cyanoborohydrideHCID 22018600N-(t-butoxycarbonyl)-N-(2-pyridinylmethyl)-N'-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

Product 1

HCID 22018852HCID 22018852, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of N-(t-butyloxycarbonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (0.206 g, 0.449 mmol) in anhydrous methanol (10 mL), at room temperature, was added furfural (0.19 mL, 2.29 mmol) followed by NaBH3CN (0.070 g, 1.11 mmol) and the resultant solution was stirred at room temperature overnight. The solvent was removed under reduced pressure and CH2Cl2 (20 mL) and 1.0 M aqueous NaOH (10 mL) were added to the residue. The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×10 mL). The combined organic phases were dried (Na2SO4) and concentrated. Purification of the crude material by column chromatography silica gel (25:1 CH2Cl2-MeOH) provided 0.103 g of the protected amine as a yellow oil.

Workup

  1. customThe solvent was removed under reduced pressure and CH2Cl2 (20 mL) and 1.0 M aqueous NaOH (10 mL)
  2. additionwere added to the residue
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with CH2Cl2 (3×10 mL)
  5. dry with materialThe combined organic phases were dried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification of the crude material by column chromatography silica gel (25:1 CH2Cl2-MeOH)

Sources & evidence

ORD record
ord-75ed2fbe24754722822e8918795bafbe
Source dataset
uspto-grants-2007_02
Patent number
US07183273B2

Reaction notes

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