p-Toluenesulfonic acid monohydrate → HCID 86601088, compound

HRID 902977Notes

Reaction equation

HRID 902977 reaction equation
C([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][C:14]2[CH:26]=[CH:25][C:24]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17](=[O:27])[C:16]=3[CH:15]=2)[CH2:9]1)(OC(C)(C)C)=O.O.[C:29]1([CH3:39])[CH:34]=[CH:33][C:32]([S:35]([OH:38])(=[O:37])=[O:36])=[CH:31][CH:30]=1>CCOC(C)=O>[C:29]1([CH3:39])[CH:30]=[CH:31][C:32]([S:35]([OH:38])(=[O:36])=[O:37])=[CH:33][CH:34]=1.[NH:8]1[CH2:12][CH2:11][C@H:10]([O:13][C:14]2[CH:26]=[CH:25][C:24]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17](=[O:27])[C:16]=3[CH:15]=2)[CH2:9]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 57439858HCID 57439858, compound

Product 1

HCID 86601088HCID 86601088, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-[(S)-N-Boc-pyrrolidin-3-yloxy]-fluoren-9-one (315 mg, 0.863 mmol; Example 4A) and p-toluenesulfonic acid monohydrate (165 mg, 0.868 mmol; Aldrich) in EtOAc (15 mL) was heated to reflux. A precipitate began to form after about 30 min of heating. After 18 h, the mixture was cooled to room temperature and the yellow crystals were collected by filtration to afford the title compound (334 mg, 0.763 mmol; 88% yield): 1H NMR (300 MHz, CD3OD) δ ppm 7.67-7.73 (m, J=8 Hz, 2H), 7.55-7.63 (m, 3H), 7.52 (dt, J=7, 1 Hz, 1H), 7.27 (dt, J=7, 1 Hz, 1H), 7.20-7.24 (m, J=5, 3 Hz, 3H), 7.14 (dd, J=8, 3 Hz, 1H), 5.24-5.30 (m, 1H), 3.44-3.63 (m, 4H), 2.29-2.39 (m, 5H); MS (DCl/NH3) m/z 266 (M+H)+; Anal. C17H15NO2.C7H8O3S: C, H, N.

Workup

  1. customto form after about 30 min
  2. temperatureof heating
  3. filtrationthe yellow crystals were collected by filtration

Sources & evidence

ORD record
ord-52768b6f5d4b4c7ead8e2055954a754d
Source dataset
uspto-grants-2008_04
Patent number
US07365193B2

Reaction notes

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