Imidazole → (S)-5-(((tert-Butyldimethylsilyl)oxy)methyl)pyrrolidin-2-one

HRID 409790Notes

Reaction equation

HRID 409790 reaction equation
[OH:1][CH2:2][C@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.N1C=CN=C1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>C(Cl)Cl>[Si:14]([O:1][CH2:2][C@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 643511(S)-5-(Hydroxymethyl)-2-pyrrolidinone

Product 1

HCID 10263224(S)-5-(((tert-Butyldimethylsilyl)oxy)methyl)pyrrolidin-2-oneYield 83.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-5-(hydroxymethyl)pyrrolidin-2-one (30.0 g, 261 mmol) and imidazole (23.1 g, 340 mmol) in DCM (900 mL) was added TBS-Cl (42.9 g, 288 mmol). The reaction mixture was stirred at RT for 30 min and filtered. The filtrate was washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified on silica gel column using a mixture of EtOAc and hexanes to give (S)-5-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-2-one (50 g, 83.7%). LRMS (M+H+) m/z 230.2.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified on silica gel column
  7. additiona mixture of EtOAc and hexanes

Sources & evidence

ORD record
ord-3cb8576182304a4b8f37b29d329b30e2
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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