Water → HCID 59291400, compound

HRID 383941Notes

Reaction equation

HRID 383941 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1([OH:18])[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]1)C.[Li+].[BH4-].O>C1COCC1>[OH:18][C:6]1([CH2:5][CH2:4][OH:3])[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:7]1

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 59291567HCID 59291567, compound

Product 1

HCID 59291400HCID 59291400, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 3-(2-ethoxy-2-oxoethyl)-3-hydroxypyrrolidine-1-carboxylate (6.35 g) in THF (100 mL) was added LiBH4 (1.01 g), followed by heating under reflux for 4 hours. The reaction mixture was cooled to room temperature, then added with water, and extracted with EtOAc. The organic layer was washed with water and brine in this order, dried over MgSO4, and then concentrated under reduced pressure to obtain tert-butyl 3-hydroxy-3-(2-hydroxyethyl)pyrrolidine-1-carboxylate (4.72 g) as a colorless oily substance.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 4 hours
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water and brine in this order
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-806de0a2d3c24896a7889b309d981c36
Source dataset
uspto-grants-2013_02
Patent number
US08367696B2

Reaction notes

Loading…