Methanol → HCID 19095905, compound

HRID 486768Notes

Reaction equation

HRID 486768 reaction equation
C[Si](C)(C)[NH:3][Si](C)(C)C.CO.[C:12]([O:16][C:17]([N:19]1[CH2:53][CH2:52][CH2:51][C:21]2([CH2:50][CH2:49][N:24]3[C:25]4[C:30]([C:31]([C:32]5[C:33](=[O:48])O[C:35](=[O:47])[C:36]=5[C:37]5[C:45]6[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=6)[N:39]([CH3:46])[CH:38]=5)=[C:23]3[CH2:22]2)=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].O>CN(C=O)C>[C:12]([O:16][C:17]([N:19]1[CH2:53][CH2:52][CH2:51][C:21]2([CH2:50][CH2:49][N:24]3[C:25]4[C:30]([C:31]([C:32]5[C:33](=[O:48])[NH:3][C:35](=[O:47])[C:36]=5[C:37]5[C:45]6[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=6)[N:39]([CH3:46])[CH:38]=5)=[C:23]3[CH2:22]2)=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 13838HexamethyldisilazaneHCID 19095892HCID 19095892, compound

Product 1

HCID 19095905HCID 19095905, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.08 g of 1,1,1,3,3,3-hexamethyldisilazane and 0.11 g of methanol was added to a solution of 380 mg of 3-[1-(tert.butoxycarbonyl)-7',9'-dihydrospiro[piperidine-3,8'(6'H)-pyrido[1,2-a]indol]-10'-yl]-4-(1-methyl-3-indolyl)furan-2,5-dione in 10 ml of DMF and the mixtue was stirred for 16 hours and subsequently poured into 50 ml of water. The resulting mixture was extracted with dichloromethane and the extracts were washed with sodium chloride solution, dried and concentrated. Chromatography of the residue on silica gel using dichloromethane/methanol (9:1) for the elution gave 220 mg of 3-[1-(tert.butoxycarbonyl)-7',9'-dihydrospiro[piperidine-3,8'(6'H)-pyrido[1,2-a]indol]-10'-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione.

Workup

  1. extractionThe resulting mixture was extracted with dichloromethane
  2. washthe extracts were washed with sodium chloride solution
  3. customdried
  4. concentrationconcentrated
  5. washfor the elution

Sources & evidence

ORD record
ord-69ead58b387146729c3907051b220a26
Source dataset
uspto-grants-1994_03
Patent number
US05292747

Reaction notes

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