Sodium Sulfate → 2Acetamido-2-{2-[4-(1,1-ethylenedioxy-5-phenylpentyl)phenyl]ethyl}propane-1,3-diol

HRID 323813Notes

Reaction equation

HRID 323813 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([NH:10][C:11]([CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2([O:44][CH2:43][CH2:42][O:41]2)[CH2:31][CH2:32][CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:26][CH:25]=1)([C:17](OCC)=[O:18])[C:12](OCC)=[O:13])(=[O:9])[CH3:8].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[C:7]([NH:10][C:11]([CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2([O:41][CH2:42][CH2:43][O:44]2)[CH2:31][CH2:32][CH2:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)=[CH:26][CH:25]=1)([CH2:17][OH:18])[CH2:12][OH:13])(=[O:9])[CH3:8]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21026720Diethyl 2-acetamido-2-{2-[4-(1,1-ethylenedioxy-5-phenylpentyl)phenyl]ethyl}malonateHCID 21226445Aluminium lithium hydride

Product 1

HCID 210267212Acetamido-2-{2-[4-(1,1-ethylenedioxy-5-phenylpentyl)phenyl]ethyl}propane-1,3-diolYield 49.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium aluminum hydride (2.0 g) in tetrahydrofuran (100 ml) was dropwise added a solution of diethyl 2-acetamido-2-{2-[4-(1,1-ethylenedioxy-5-phenylpentyl)phenyl]ethyl}malonate (14.0 g) in tetrahydrofuran (50 ml) at 3-13° C. over 30 minutes, and the mixture was stirred at room temperature for 2 hours. To the reaction mixture was dropwise added a saturated aqueous sodium sulfate solution (27 ml), and the mixture was stirred at room temperature for an hour. The precipitate was filtered through celite and the filtrate was concentrated under reduced pressure to give a colorless transparent oily substance (11.7 g). The obtained colorless transparent oily substance was purified by silica gel column chromatography (eluent; chloroform:methanol=20:1) to give 2acetamido-2-{2-[4-(1,1-ethylenedioxy-5-phenylpentyl)phenyl]ethyl}propane-1,3-diol (5.8 g) as a colorless transparent oily substance.

Workup

  1. stirringthe mixture was stirred at room temperature for an hour
  2. filtrationThe precipitate was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto give a colorless transparent oily substance (11.7 g)
  5. customThe obtained colorless transparent oily substance was purified by silica gel column chromatography (eluent; chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-884357bd54c94e45a0555b328f3ec186
Source dataset
uspto-grants-2001_04
Patent number
US06214873B1

Reaction notes

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