3-Furaldehyde → HCID 11683799, compound

HRID 733393Notes

Reaction equation

HRID 733393 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[CH:9][C:10]3[CH:11]([CH:21]4[CH2:27][CH:26]5[NH:28][CH:23]([CH2:24][CH2:25]5)[CH2:22]4)[C:12]4[C:17]([O:18][C:19]=3[CH:20]=2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:2]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C.[O:47]1[CH:51]=[CH:50][C:49]([CH:52]=O)=[CH:48]1>C(Cl)CCl.C(Cl)Cl>[O:47]1[CH:51]=[CH:50][C:49]([CH2:52][N:28]2[CH:23]3[CH2:24][CH2:25][CH:26]2[CH2:27][CH:21]([CH:11]2[C:10]4[CH:9]=[CH:8][C:7]([C:3]5[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=5)=[CH:20][C:19]=4[O:18][C:17]4[C:12]2=[CH:13][CH:14]=[CH:15][CH:16]=4)[CH2:22]3)=[CH:48]1

Participants

6

Reactant 3

HCID 103513-FuraldehydeHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)HCID 57839257HCID 57839257, compound2×

Product 1

HCID 11683799HCID 11683799, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(3-pyridin-3-yl-9H-xanthen-9-yl)-8-aza-bicyclo[3.2.1]octane, 3b (0.08 g, 0.134 mmol) in ClCH2CH2Cl (2 mL) was added tetramethyl-ammonium triacetoxyborohydride (0.053 g, 2.01 mmol) and 3-furaldehyde (0.17 mL, 2.0 mmol). The reaction was stirred at rt for 24 h. The reaction was 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 via reverse phase chromatography (eluent: CH3CN in H2O containing 0.1% TFA) to yield 0.045 g (75%) of title compound 8-furan-3-ylmethyl-3-(3-pyridin-3-yl-9H-xanthen-9-yl)-8-aza-bicyclo[3.2.1]-octane, 4b as a TFA salt. MS m/z=449.1 (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 via reverse phase chromatography (eluent: CH3CN in H2O containing 0.1% TFA)

Sources & evidence

ORD record
ord-67837b26cafa40fc84a07e2ea2dd955a
Source dataset
uspto-grants-2009_09
Patent number
US07589104B2

Reaction notes

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