Tetrahydrofuran → HCID 5373233, compound

HRID 1757935Notes

Reaction equation

HRID 1757935 reaction equation
O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:12][CH:13]1[CH:38]2O[C:37]2([CH3:40])[CH:36]([OH:41])[CH2:35][C:33](=[O:34])[N:32]([CH3:42])[C:25]2=[C:26]([Cl:31])[C:27]([O:29][CH3:30])=[CH:28][C:23](=[CH:24]2)[CH2:22][C:21]([CH3:43])=[CH:20][CH:19]=[CH:18][CH:17]([O:44][CH3:45])[C:16]2([OH:50])[NH:46][C:47]([O:49][CH:14]1[CH2:15]2)=[O:48]>[Cl-].[Cl-].[Cl-].[Ti+3].O>[CH3:12][CH:13]1[CH:14]2[O:49][C:47]([NH:46][C:16]([OH:50])([CH2:15]2)[CH:17]([O:44][CH3:45])[CH:18]=[CH:19][CH:20]=[C:21]([CH3:43])[CH2:22][C:23]2=[CH:24][C:25](=[C:26]([Cl:31])[C:27]([O:29][CH3:30])=[CH:28]2)[N:32]([CH3:42])[C:33](=[O:34])[CH2:35][CH:36]([OH:41])[C:37]([CH3:40])=[CH:38]1)=[O:48]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 5358230HCID 5358230, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 5373233HCID 5373233, compoundYield 45.3%

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 962WaterSolvent

Procedure

To 6 ml of dried tetrahydrofuran (THF) is added 321 mg of anhydrous titanium trichloride, and the mixture is stirred at room temperature in dry nitrogen atmosphere for 15 minutes while adding thereto portionwise 20 mg of lithium aluminum hydride (LAH). Thereafter, 50 mg of maytansinol is added, and the mixture is stirred at room temperature for about 30 minutes. Then, 15 ml of water is added, and the reaction mixture is extracted with chloroform, and the organic layer is washed with water and dried over anhydrous sodium sulfate. The chloroform is distilled off under reduced pressure, and the residue is purified by silica gel column chromatography [silica gel (Merck) Art 7736; solvent system: chloroform:methanol=100:1.5] to give 22 mg of 4,5-deoxymaytansinol. Yield=45.1%. Mass spectrum (m/e): 548 (M+), 530, 487.

Workup

  1. additionwhile adding
  2. stirringthe mixture is stirred at room temperature for about 30 minutes
  3. extractionthe reaction mixture is extracted with chloroform
  4. washthe organic layer is washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe chloroform is distilled off under reduced pressure
  7. customthe residue is purified by silica gel column chromatography [silica gel (Merck) Art 7736; solvent system: chloroform:methanol=100:1.5]

Sources & evidence

ORD record
ord-c7c6289c4ecf460e97e97346c331d626
Source dataset
uspto-grants-1983_02
Patent number
US04371533

Reaction notes

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