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

HRID 2279466Notes

Reaction equation

HRID 2279466 reaction equation
[OH:1][C@@H:2]([CH3:7])[C:3](OC)=[O:4].[NH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1>>[OH:1][C@@H:2]([CH3:7])[C:3]([N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:4]

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 94386methyl (S)-lactate

Product 1

HCID 11051776(2S)-2-hydroxy-1-(1-pyrrolidinyl)-1-propanoneYield 99.7%

Procedure

(S)-Methyl 2-hydroxypropanoate (30.0 g, 288 mmol) and pyrrolidine (22.5 g, 317 mmol) were stirred at RT for 3 d. The crude product was purified by passing through a SiO2 plug eluting with 80% EtOAc/hexane to afford 41.1 g (99.6%) (S)-2-hydroxy-1-(pyrrolidin-1-yl)propan-1-one (108).

Workup

  1. customThe crude product was purified
  2. washeluting with 80% EtOAc/hexane

Sources & evidence

ORD record
ord-fe1ba449fc2b4abe88e5ee84c5516a65
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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