Methanol → HCID 19095906, compound

HRID 486774Notes

Reaction equation

HRID 486774 reaction equation
C[Si](C)(C)[NH:3][Si](C)(C)C.CO.[C:12]([O:16][C:17]([N:19]1[CH2:51][CH2:50][C:21]2([CH2:49][N:24]3[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=4[C:31]([C:32]4[C:33](=O)[O:34][C:35](=[O:47])[C:36]=4[C:37]4[C:45]5[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=5)[N:39]([CH3:46])[CH:38]=4)=[C:23]3[CH2:22]2)[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]>CN(C=O)C>[C:12]([O:16][C:17]([N:19]1[CH2:51][CH2:50][C:21]2([CH2:49][N:24]3[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=4[C:31]([C:32]4[C:33](=[O:34])[NH:3][C:35](=[O:47])[C:36]=4[C:37]4[C:45]5[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=5)[N:39]([CH3:46])[CH:38]=4)=[C:23]3[CH2:22]2)[CH2:20]1)=[O:18])([CH3:14])([CH3:13])[CH3:15]

Participants

5

Reactant 3

HCID 887MethanolHCID 13838HexamethyldisilazaneHCID 19095911HCID 19095911, compound

Product 1

HCID 19095906HCID 19095906, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.59 ml of 1,1,1,3,3,3-hexamethyldisilazane and 45 mg of methanol was added to a solution of 150 mg of 3-[1-(tert.butoxy-carbonyl)-1',3'-dihydrospiro[pyrrolidine-3,2'-pyrrolo[1,2-a]indol]-9'-yl]-4-(1-methyl-3-indolyl)-furan-2,5-dione in 10 ml of DMF and stirred for 72 hours. The solvent was removed by evaporation and the residue was treated with 10 ml of methanol. After evaporation, the residue was subjected to chromatography on silica gel using dichloromethane/ethyl acetate (4:1) for the elution. There were obtained 120 mg of 3-[1-(tert.butoxycarbonyl)-1',3'-dihydrospiro[pyrrolidine-3,2'-pyrrolo[1,2-a]indol]-9'-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione of melting point 232°-235° C.

Workup

  1. customThe solvent was removed by evaporation
  2. additionthe residue was treated with 10 ml of methanol
  3. customAfter evaporation
  4. washfor the elution

Sources & evidence

ORD record
ord-40352807988843ab824a05561f4f43a2
Source dataset
uspto-grants-1994_03
Patent number
US05292747

Reaction notes

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