Benzyl Chloride → (R)-(+)-1-Benzyl-3-pyrrolidinol

HRID 2375446Notes

Reaction equation

HRID 2375446 reaction equation
Cl.[NH:2]1[CH2:6][CH2:5][C@@H:4]([OH:7])[CH2:3]1.C(N(CC)CC)C.[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>ClCCl.C(Cl)(Cl)Cl.[OH-].[Na+]>[CH2:15]([N:2]1[CH2:6][CH2:5][C@@H:4]([OH:7])[CH2:3]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 7503Benzyl ChlorideHCID 8471TriethylamineHCID 2759336(3R)-pyrrolidin-3-ol hydrochloride

Product 1

HCID 643472(R)-(+)-1-Benzyl-3-pyrrolidinolYield 44.4%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

The compound (3R)-pyrrolidin-3-ol hydrochloride (2.2 g, 17.8 mM) was dissolved in dichloromethane (25.0 ml) and triethylamine (5.0 ml, 35.6 mM) was added at room temperature with constant stirring for 5 minutes. Benzyl chloride (2.5 ml, 21.4 mM) was added to it in one lot at the same temperature followed by refluxing for 15 hours. The reaction mixture was diluted with chloroform and 1N sodium hydroxide (15.0 ml) was added with constant stirring for 10 minutes. The organic layer was separated and washed with aqueous sodium bicarbonate and brine solution. It was further dried over anhydrous sodium sulphate and concentrated to get the title compound. Yield=44.4% (1.4 g, 7.9 mM).

Workup

  1. temperatureby refluxing for 15 hours
  2. additionwas added
  3. stirringwith constant stirring for 10 minutes
  4. customThe organic layer was separated
  5. washwashed with aqueous sodium bicarbonate and brine solution
  6. dry with materialIt was further dried over anhydrous sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cc1bc2513c7f4f9b8e9d27fe6f744c67
Source dataset
uspto-grants-2008_12
Patent number
US07465751B2

Reaction notes

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