Ethanol → Benzyl (3S)-3-hydroxypyrrolidine-1-carboxylate

HRID 2246229Notes

Reaction equation

HRID 2246229 reaction equation
C([O:4][C@H:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6]1)(=O)C.C(O)C.[OH-].[K+]>O>[OH:4][C@H:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 15086785HCID 15086785, compound

Product 1

HCID 13438604Benzyl (3S)-3-hydroxypyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a 20-L, three neck round bottom flask containing 427 g (1.62 mol) of benzyl (3S)-3-acetoxypyrrolidine-1-carboxylate was added 4 L of absolute ethanol followed by 101 g (1.57 mol) of potassium hydroxide in about 400 mL of water. After about 15 min, the reaction mixture was poured into 8 L of water and extracted with 8 L of ethyl acetate. The aqueous layer was then extracted with an additional 4 L of ethyl acetate. The combined organics were washed with saturated aqueous brine, dried over magnesium sulfate and concentrated to a thick oil and solids.

Workup

  1. extractionextracted with 8 L of ethyl acetate
  2. extractionThe aqueous layer was then extracted with an additional 4 L of ethyl acetate
  3. washThe combined organics were washed with saturated aqueous brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to a thick oil and solids

Sources & evidence

ORD record
ord-c635402f2d354c488439bb75b87e8cfd
Source dataset
uspto-grants-2010_03
Patent number
US07687492B2

Reaction notes

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