Ethanol → (S)-3-((R)-2-Ethoxy-1-hydroxyethyl)pyrrolidine-1-carboxylic Acid t-Butyl Ester

HRID 2390570

Reaction equation

HRID 2390570 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([C@@H:13]2[CH2:15][O:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O-][CH2:17][CH3:18].[Na+].CC[OH:22]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([C@@H:13]([OH:22])[CH2:15][O:14][CH2:17][CH3:18])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 86650334(S)-(R)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester

Product 1

HCID 66858889(S)-3-((R)-2-Ethoxy-1-hydroxyethyl)pyrrolidine-1-carboxylic Acid t-Butyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)—(R)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester (440 mg, 2.1 mmol) was added to 2M of sodium ethoxide in EtOH (2.1 mL, 4.1 mmol; prepared from EtOH and NaH). The resulting solution was placed in a microwave reactor for 10 minutes at 100° C., then cooled to room temperature. DCM (5 mL) was added, followed by washing with saturated aqueous NaCl (5 mL). The organic layer was collected, dried over Na2SO4, filtered, and concentrated. The crude product was purified by column chromatography (0-100% ether/Hexanes) to give the title compound as a clear oil (400 mg).

Workup

  1. washby washing with saturated aqueous NaCl (5 mL)
  2. customThe organic layer was collected
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (0-100% ether/Hexanes)

Sources & evidence

ORD record
ord-38406471dfb1477c8ba059f1fe35e950
Source dataset
uspto-grants-2012_09
Patent number
US08273786B2

Linked notes

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