Water → HCID 15518230, compound

HRID 635524Notes

Reaction equation

HRID 635524 reaction equation
[CH2:1]1[O:42][C:4]2=[CH:5][C:6]3[C:19]4[C:10](=[C:11]5[C:16](=[C:17]([CH2:20][CH2:21][CH2:22][O:23][Si](C(C)(C)C)(C)C)[N:18]=4)[C:15]([O:31][CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[C:14]([O:39][CH3:40])[CH:13]=[CH:12]5)[CH:9]=[CH:8][C:7]=3[CH:41]=[C:3]2[O:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[CH2:1]1[O:42][C:4]2=[CH:5][C:6]3[C:19]4[C:10](=[C:11]5[C:16](=[C:17]([CH2:20][CH2:21][CH2:22][OH:23])[N:18]=4)[C:15]([O:31][CH2:32][C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)=[C:14]([O:39][CH3:40])[CH:13]=[CH:12]5)[CH:9]=[CH:8][C:7]=3[CH:41]=[C:3]2[O:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 11721210HCID 11721210, compound

Product 1

HCID 15518230HCID 15518230, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After 2,3-(methylenedioxy)-6-[3-(t-butyldimethylsiloxy)propyl]-7-benzyloxy-8-methoxy-benzo[c]phenanthridine (374.4 mg, 0.644 mmol) was dissolved in tetrahydrofuran (3.2 mL), tetrabutylammonium fluoride (1M tetrahydrofuran solution, 1.9 mL) was added to the solution. The mixture was stirred overnight at room temperature. Water was added to the reaction mixture followed by extraction with methylene chloride. The organic phase was dried over anhydrous sodium sulfate and then concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (eluted with methylene chloride) to provide 2,3-(methylenedioxy)-6-(3-hydroxypropyl)-7-benzyloxy-8-methoxy-benzo[c]phenanthridine (263.7 mg, yield 88%) as colorless powders.

Workup

  1. extractionfollowed by extraction with methylene chloride
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by silica gel column chromatography (eluted with methylene chloride)

Sources & evidence

ORD record
ord-efa177ef82d940b599637e7ddfb2cf49
Source dataset
uspto-grants-2001_02
Patent number
US06187783B1

Reaction notes

Loading…