Acetic Acid → HCID 11522352, compound
Reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:15])[C:4]=2[CH:3]=1.S([O-])([O-])(=O)=O.[Na+].[Na+].C(O[BH-](O[C:33](=O)[CH3:34])OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[Na+].[Na+].[C:43](O)(=O)[CH3:44]>>[N:1]12[CH2:34][CH2:33][CH:4]([CH2:43][CH2:44]1)[CH:3]([NH:1][C:2]1[CH:14]=[CH:13][C:12]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5](=[O:15])[C:4]=3[CH:3]=1)[CH2:2]2Participants
Procedure
A suspension of 2-aminofluoren-9-one (400 mg, 2.05 mmol; Aldrich) and anhydrous sodium sulfate (3.0 g, 21 mmol; EM Science) in acetic acid (10 mL) was stirred for 15 min and then treated with sodium triacetoxyborohydride (1.3 g, 6.13 mmol; Aldrich). After stirring overnight, the reaction mixture was basified with saturated aqueous Na2CO3 and extracted with EtOAc (3×). The combined organic phases were concentrated under vacuum and purified by flash chromatography (80 g silica gel, 1-16% gradient of NH4OH-MeOH (1:10) in CH2Cl2) to afford the title compound (492 mg, 1.62 mmol; 79% yield): 1H NMR (300 MHz, CD3OD) δ ppm 7.35-7.47 (m, 3H), 7.33 (d, J=8 Hz, 1H), 7.11 (td, J=7, 2 Hz, 1H), 6.86 (d, J=2 Hz, 1H), 6.70 (dd, J=8, 2 Hz, 1H), 3.57-3.67 (m, 1H), 3.32-3.40 (m, 1H), 2.74-3.00 (m, 4H), 2.60 (ddd, J=14, 5, 1 Hz, 1H), 1.67-2.06 (m, 4H), 1.41-1.55 (m, 1H); MS (DCl/NH3) m/z 305 (M+H)+.
Workup
- stirringAfter stirring overnight
- extractionextracted with EtOAc (3×)
- concentrationThe combined organic phases were concentrated under vacuum
- custompurified by flash chromatography (80 g silica gel, 1-16% gradient of NH4OH-MeOH (1:10) in CH2Cl2)
Sources & evidence
- ORD record
- ord-9fe52cfbcc2c420685e4e7449c1881f7
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07365193B2
Reaction notes
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