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

HRID 1795709Notes

Reaction equation

HRID 1795709 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

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 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
  5. customwas purified by silica gel column chromatography (eluent; chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-f9c120dd94a2445e86f008aaefbb8760
Source dataset
uspto-grants-2006_04
Patent number
USRE039072E1

Reaction notes

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