Tetrahydrofuran → HCID 10178900, compound

HRID 2253702Notes

Reaction equation

HRID 2253702 reaction equation
[C:1]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])[CH:12]1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(OCC)=[O:2].C1COCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[OH:2][CH2:1][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])[CH:12]1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 18533781HCID 18533781, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10178900HCID 10178900, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Under a nitrogen atmosphere in a round-bottom flask were placed 95 mg (0.22 mmol) of the title compound of Example 97 and 1 ml of THF. The system was cooled in an ice/acetone bath, 0.44 ml (0.44 mmol) of 1M lithium aluminum hydride in ether was added to the system and the mixture was stirred for 10 minutes. The cold bath was removed, the mixture was stirred at room temperature for 20 minutes and the cold bath was replaced. To the system was added cautiously ca. 0.4 ml of 2M aqueous sodium hydroxide, and the mixture was stirred at room temperature for 20 minutes. Sodium sulfate was added to the system, the mixture was stirred for 30 minutes, solids were removed by suction filtration and the filtrate was concentrated. The crude material was purified by flash column chromatography (5 g of silica gel) using 3:47 methanol/chloroform as the eluant to obtain 49 mg of the title compound.

Workup

  1. customUnder a nitrogen atmosphere in a round-bottom flask were placed
  2. temperatureThe system was cooled in an ice/acetone bath
  3. customThe cold bath was removed
  4. stirringthe mixture was stirred at room temperature for 20 minutes
  5. additionTo the system was added cautiously ca. 0.4 ml of 2M aqueous sodium hydroxide
  6. stirringthe mixture was stirred at room temperature for 20 minutes
  7. additionSodium sulfate was added to the system
  8. stirringthe mixture was stirred for 30 minutes
  9. customsolids were removed by suction filtration
  10. concentrationthe filtrate was concentrated
  11. customThe crude material was purified by flash column chromatography (5 g of silica gel)

Sources & evidence

ORD record
ord-466a59d07233443b89cc1334894177d4
Source dataset
uspto-grants-1993_08
Patent number
US05232929

Reaction notes

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