Methanol → HCID 19095952, compound

HRID 486764Notes

Reaction equation

HRID 486764 reaction equation
C[Si](C)(C)[NH:3][Si](C)(C)C.CO.[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][C:21]2([CH2:52][CH2:51][N:26]3[C:27]4[C:32]([C:33]([C:34]5[C:35](=[O:50])O[C:37](=[O:49])[C:38]=5[C:39]5[C:47]6[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=6)[N:41]([CH3:48])[CH:40]=5)=[C:25]3[CH2:24]2)=[CH:31][CH:30]=[CH:29][CH:28]=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[CH2:23][CH2:22][C:21]2([CH2:52][CH2:51][N:26]3[C:27]4[C:32]([C:33]([C:34]5[C:35](=[O:50])[NH:3][C:37](=[O:49])[C:38]=5[C:39]5[C:47]6[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=6)[N:41]([CH3:48])[CH:40]=5)=[C:25]3[CH2:24]2)=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:20]1)=[O:18])([CH3:13])([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 13838HexamethyldisilazaneHCID 19095966HCID 19095966, compound

Product 1

HCID 19095952HCID 19095952, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4.09 g of 1,1,1,3,3,3-hexamethyldisilazane and 0.41 g of methanol was added to a solution of 1.40 g of 3-[1'-(tert.butoxycarbonyl)-7,9-dihydrospiro[pyrido[1,2-a]indole-8(6H),3'-pyrrolidin]-10-yl]-4-(1-methyl-3-indolyl)furan-2,5-dione in 25 ml of dry DMF and stirred for 16 hours. The mixture was poured into 100 ml of water and extracted with ethyl acetate. The ethyl acetate extracts were washed with sodium chloride solution, dried and concentrated. There were obtained 820 mg of 3-[1'-(tert.butoxycarbonyl)-7,9-dihydrospiro[pyrido-[1,2-a]indole-8(6H).3'-pyrrolidin]-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione after chromatography on silica gel using dichloromethane/methanol (9:1) for the elution.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate extracts were washed with sodium chloride solution
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f45da85435024cd6b61b1170aa4375f6
Source dataset
uspto-grants-1994_03
Patent number
US05292747

Reaction notes

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