Pyrrolidine → (2S)-2-hydroxy-1-(1-pyrrolidinyl)-1-propanone

HRID 631761Notes

Reaction equation

HRID 631761 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.C[O:7][C:8](=O)[C@H:9]([CH3:11])[OH:10]>>[OH:10][C@@H:9]([CH3:11])[C:8]([N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:7]

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 94386methyl (S)-lactate

Product 1

HCID 11051776(2S)-2-hydroxy-1-(1-pyrrolidinyl)-1-propanoneYield 84.4%

Procedure

Pyrrolidine (39.25 g, 0.48 mole) was added dropwise to methyl-(S)-(−)-lactate (25.0 g, 0.24 mol) at 0° C. and the reaction mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated under reduced pressure and purified with distillation to afford (2S)-2-hydroxy-1-(pyrrolidin-1-yl)propan-1-one 2 (29.0 g, 84%) at 150° C.-160° C. as light yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. distillationpurified with distillation

Sources & evidence

ORD record
ord-fafa1e56c82c4d9db4286c2715c213ac
Source dataset
uspto-grants-2016_04
Patent number
US09321716B1

Reaction notes

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