Tetrahydrofuran → HCID 19431937, compound

HRID 1077561Notes

Reaction equation

HRID 1077561 reaction equation
C(OC([C:7]1[N:8]=[CH:9][C:10]2[N:11]([S:31]([C:34]3[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=3)(=[O:33])=[O:32])[C:12]3[C:17]([C:18]=2[C:19]=1[CH2:20][O:21][CH3:22])=[CH:16][C:15]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[CH:14][CH:13]=3)=O)(C)C.C[Li].[Cl-].[NH4+].[O:45]1CC[CH2:47][CH2:46]1>>[CH2:24]([O:23][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[N:11]([S:31]([C:34]1[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=1)(=[O:32])=[O:33])[C:10]1[CH:9]=[N:8][C:7]([C:46](=[O:45])[CH3:47])=[C:19]([CH2:20][O:21][CH3:22])[C:18]2=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 53671227HCID 53671227, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 19431937HCID 19431937, compound

Conditions

Temperature
-60 °C

Procedure

8.4 g of 6-benzyloxy-4-methoxymethyl-9-tosyl-β-carboline-3-carboxylic acid isopropyl ester is dissolved in 500 ml absolute tetrahydrofuran and cooled to -60° C. 15 ml of a 1.5 molar ethereal methyllithium solution is added drop by drop to this solution under argon atmosphere and then stirred for another 4 hours at -60° C. After heating to room temperature the reaction solution is mixed with saturated ammonium chloride solution, extracted with methylene chloride, dried and concentrated by evaporation. The resulting crude product is chromatographed on silica gel with cyclohexane: ethyl acetate=8:2. 4.1 g of 6-benzyloxy-4-methoxymethyl-3-acetyl-9-tosyl-β-carboline with a melting point of 173-175° C. is obtained.

Workup

  1. temperatureAfter heating to room temperature the reaction solution
  2. extractionextracted with methylene chloride
  3. customdried
  4. concentrationconcentrated by evaporation
  5. customThe resulting crude product is chromatographed on silica gel with cyclohexane

Sources & evidence

ORD record
ord-45753da0e41042199c9acaf55d68c77f
Source dataset
uspto-grants-1996_08
Patent number
US05543519

Reaction notes

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