Chloroform → [(3S,4S)-1-benzyl-4-(hydroxymethyl)pyrrolidin-3-yl]methanol

HRID 1479307Notes

Reaction equation

HRID 1479307 reaction equation
[CH2:1]([N:8]1[CH2:12][C@@H:11]([C:13](OCC)=[O:14])[C@H:10]([C:18](OCC)=[O:19])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].C(Cl)(Cl)Cl>C1COCC1>[CH2:1]([N:8]1[CH2:12][C@@H:11]([CH2:13][OH:14])[C@H:10]([CH2:18][OH:19])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 62649Sodium sulfate decahydrateHCID 6558921diethyl (3S,4S)-1-benzylpyrrolidine-3,4-dicarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 13814312[(3S,4S)-1-benzyl-4-(hydroxymethyl)pyrrolidin-3-yl]methanolYield 93.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

trans-Diethyl 1-benzylpyrrolidine-3,4-dicarboxylate (830 mg, 2.72 mmol) synthesized by using WO2009/027820 as a reference was dissolved in THF (24 mL). After adding lithium aluminum hydride (206 mg, 5.44 mmol) at 0° C., the solution was stirred at room temperature for 1.3 hours. The reaction mixture was further stirred at room temperature after adding sodium sulfate decahydrate, chloroform, and Celite. The mixture was filtered after adding anhydrous magnesium sulfate, and the filtrate was concentrated under reduced pressure. Hexane was added, and the solid was removed by filtration to give (trans-1-benzylpyrrolidine-3,4-diyl)dimethanol (565 mg, 93.9%).

Workup

  1. stirringThe reaction mixture was further stirred at room temperature
  2. filtrationThe mixture was filtered
  3. additionafter adding anhydrous magnesium sulfate
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionHexane was added
  6. customthe solid was removed by filtration

Sources & evidence

ORD record
ord-d534b88638534b0f8cb0f2297bd4d2a6
Source dataset
uspto-grants-2016_08
Patent number
US09408914B2

Reaction notes

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