Water → (R)-4-(hydroxymethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one

HRID 2208972Notes

Reaction equation

HRID 2208972 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]([N:11]2[C:15](=[O:16])[CH2:14][C@@H:13]([C:17](O)=[O:18])[CH2:12]2)[CH3:10])=[CH:5][CH:4]=1.O.CCOC(C)=O>C1COCC1>[OH:18][CH2:17][C@H:13]1[CH2:12][N:11]([C@@H:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH3:10])[C:15](=[O:16])[CH2:14]1

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 94274988(R)-1-((R)-1-(4-methoxyphenyl)ethyl)-5-oxopyrrolidine-3-carboxylic acid

Product 1

HCID 117843430(R)-4-(hydroxymethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-1-((R)-1-(4-methoxyphenyl)ethyl)-5-oxopyrrolidine-3-carboxylic acid 1.01 (610 mg, 2.32 mmol) in THF (6 mL) at 0° C. was added BH3-Me2S (2M, 1.74 mL, 3.48 mmol) and the reaction was stirred for 3 hours. Water and EtOAc were added, the layers were separated and the aqueous layer was extracted with EtOAc (4×25 mL). The residue was purified by flash chromatography (EtOAc→15% MeOH in EtOAc) to afford (R)-4-(hydroxymethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one 1.06.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc (4×25 mL)
  3. customThe residue was purified by flash chromatography (EtOAc→15% MeOH in EtOAc)

Sources & evidence

ORD record
ord-ad5c834b8d3149fb94145b4bd1df2b40
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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