Water → HCID 21462981, compound

HRID 1940543Notes

Reaction equation

HRID 1940543 reaction equation
O[C:2]1([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[CH:15]=[CH:14]3)[CH2:7][CH2:6][N:5]([C:8](=[O:10])[CH3:9])[CH2:4][CH2:3]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O>ClCCl>[CH:27]([Si:20]([CH:21]([CH3:23])[CH3:22])([CH:24]([CH3:26])[CH3:25])[N:16]1[C:17]2[C:13](=[CH:12][C:11]([C:2]3[CH2:7][CH2:6][N:5]([C:8](=[O:10])[CH3:9])[CH2:4][CH:3]=3)=[CH:19][CH:18]=2)[CH:14]=[CH:15]1)([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 962WaterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 21463004HCID 21463004, compound

Product 1

HCID 21462981HCID 21462981, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(4-Hydroxy-4-[1-triisopropylsilyl-1H-indol-5-yl]-piperidin-1-yl)ethanone (3.11 g, 7.4 mmol) in dichloromethane (100 ml) was treated with pyridinium p-toluenesulfonate (3.8 g, 15.1 mmol) and stirred for 72 hours. The solution was poured into water and extracted with dichloromethane (100 ml). The extractions were dried (MgSO4), concentrated and the crude product purified by flash chromatography using ethyl acetate as eluant, to give 1-(4-[1-triisopropylsilyl-1H-indol-5-yl]-1,2,3,6-tetrahydropyridin-1-yl)-ethanone (1.95 g, 66%) as a white solid; δH (CDCl3) 0.80 (18H, d, J 8.5 Hz, 6×CH3), 1.30 (3H, m, 3×CH), 1.75 (3H, d, J 6.7 Hz, COCH3), 2.30 (2H, m, tetrahydropyridinyl H), 3.25 (1H, t, J 5.6 Hz, tetrahydropyridinyl H), 3.40 (1H, t, J 5.6 Hz, tetrahydropyridinyl H), 3.75 (1H, m, tetrahydropyridyl H), 3.85 (1H, m, tetrahydropyridyl H), 5.60 (1H, m, CH=CR), 6.20 (1H, d, J 2.2 Hz, ArH), 6.80 (2H, m, ArH), 7.00 (1H, d, J 7.3 Hz, ArH), and 7.20 (1H, m, ArH).

Workup

  1. extractionextracted with dichloromethane (100 ml)
  2. extractionThe extractions
  3. dry with materialwere dried (MgSO4)
  4. concentrationconcentrated
  5. customthe crude product purified by flash chromatography

Sources & evidence

ORD record
ord-815ff5e113b8490eb7facb6aa7130a0b
Source dataset
uspto-grants-1997_12
Patent number
US05700809

Reaction notes

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