p-Toluenesulfonic acid monohydrate → HCID 86599901, compound

HRID 553026Notes

Reaction equation

HRID 553026 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[CH2:7][O:8][C:9]1[CH:21]=[CH:20][C:19]2[C:18]3[C:13](=[CH:14][C:15]([O:22][CH2:23][C@H:24]4[CH2:28][CH2:27][CH2:26][N:25]4[CH3:29])=[CH:16][CH:17]=3)[C:12](=[O:30])[C:11]=2[CH:10]=1.O.[C:32]1([CH3:42])[CH:37]=[CH:36][C:35]([S:38]([OH:41])(=[O:40])=[O:39])=[CH:34][CH:33]=1>C(OCC)(=O)C.C(O)C>[C:32]1([CH3:42])[CH:33]=[CH:34][C:35]([S:38]([OH:41])(=[O:39])=[O:40])=[CH:36][CH:37]=1.[C:32]1([CH3:42])[CH:33]=[CH:34][C:35]([S:38]([OH:41])(=[O:39])=[O:40])=[CH:36][CH:37]=1.[CH3:29][N:25]1[CH2:26][CH2:27][CH2:28][C@@H:24]1[CH2:23][O:22][C:15]1[CH:16]=[CH:17][C:18]2[C:19]3[C:11](=[CH:10][C:9]([O:8][CH2:7][C@H:3]4[CH2:4][CH2:5][CH2:6][N:2]4[CH3:1])=[CH:21][CH:20]=3)[C:12](=[O:30])[C:13]=2[CH:14]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 113157462,7-Bis[[(2R)-1-methyl-2-pyrrolidinyl]methoxy]-9H-fluoren-9-one

Product 1

HCID 86599901HCID 86599901, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 1C (50 mg, 0.12 mmol) was dissolved in ethyl acetate (5 mL) and ethanol (0.2 mL), then p-toluenesulfonic acid monohydrate (46 mg, 0.24 mmol; Aldrich) was added. After stirring the mixture for 16 hours, the resulting solid was collected by filtration to afford the title compound (68 mg, 0.09 mmol; 74%): 1H NMR (300 MHz, methanol-d4): δ 7.68 (4H, d, J=8 Hz), 7.54 (2H, d, J=8 Hz), 7.27-7.14 (8H, m), 4.46 (2H, dd, J=11, 3 Hz), 4.27 (2H, dd, J=11, 7 Hz), 3.88 (2H, m), 3.73 (2H, m), 3.35-3.19 (4H, m), 3.07 (6H, s), 2.48-1.97 (12H, m). MS (DCI/NH3): m/z 407 (M+1)+. Anal. Calcd. for C25H30N2O3.2C7H8O3S.H2O: C, 60.92; H, 6.29; N, 3.64. Found: C, 61.02; H, 6.25; N, 3.57.

Workup

  1. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-2e7e7ed81db44eb7ab0735fcc9700947
Source dataset
uspto-grants-2011_05
Patent number
US07951791B2

Reaction notes

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