3-Furaldehyde → 9-(8-Furan-3-ylmethyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-9H-xanthene-3-carboxylic acid diethylamide

HRID 733390Notes

Reaction equation

HRID 733390 reaction equation
[CH2:1]([N:3]([CH2:28][CH3:29])[C:4]([C:6]1[CH:7]=[CH:8][C:9]2[CH:10]([CH:20]3[CH2:26][CH:25]4[NH:27][CH:22]([CH2:23][CH2:24]4)[CH2:21]3)[C:11]3[C:16]([O:17][C:18]=2[CH:19]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C.[O:48]1[CH:52]=[CH:51][C:50]([CH:53]=O)=[CH:49]1>C(Cl)Cl>[CH2:28]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:7]=[CH:8][C:9]2[C:10](=[C:20]3[CH2:26][CH:25]4[N:27]([CH2:53][C:50]5[CH:51]=[CH:52][O:48][CH:49]=5)[CH:22]([CH2:23][CH2:24]4)[CH2:21]3)[C:11]3[C:16]([O:17][C:18]=2[CH:19]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:29]

Participants

5

Reactant 3

HCID 103513-FuraldehydeHCID 115166569-(8-Aza-bicyclo[3.2.1]oct-3-yl)-9H-xanthene-3-carboxylic acid diethylamide2×HCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)

Product 1

HCID 113173239-(8-Furan-3-ylmethyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-9H-xanthene-3-carboxylic acid diethylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 9-(8-aza-bicyclo[3.2.1]oct-3-yl)-9H-xanthene-3-carboxylic acid diethylamide, 9a (0.65 g, 1.7 mmol) in CH2Cl2 (20 mL) were added tetramethylammonium triacetoxyborohydride (0.53 g, 2.5 mmol) and 3-furaldehyde (0.17 mL, 2.0 mmol). The mixture was stirred at rt for 24 h, diluted with CH2Cl2 (10 mL), and washed with 1 N NaOH. The organic phase was dried over sodium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography (eluent: 5% 0.5 M NH3 in methanol in CH2Cl2) to yield title compound 9-(8-furan-3-ylmethyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-9H-xanthene-3-carboxylic acid diethylamide, 10a (0.25 g, 0.53 mmol). MS m/z=471.2 (MH+).

Workup

  1. washwashed with 1 N NaOH
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography (eluent: 5% 0.5 M NH3 in methanol in CH2Cl2)

Sources & evidence

ORD record
ord-89141a3bc2264194a82b16b8545125a5
Source dataset
uspto-grants-2009_09
Patent number
US07589104B2

Reaction notes

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