1-Ethyl-3,3-dimethyl-5-{[(triphenylmethyl)oxy]methyl}-2-pyrrolidinone → HCID 67459874, compound

HRID 554153Notes

Reaction equation

HRID 554153 reaction equation
[CH2:1]([N:3]1[CH:7]([CH2:8][O:9]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:6][C:5]([CH3:30])([CH3:29])[C:4]1=[O:31])[CH3:2]>CO>[CH2:1]([N:3]1[CH:7]([CH2:8][OH:9])[CH2:6][C:5]([CH3:30])([CH3:29])[C:4]1=[O:31])[CH3:2]

Participants

3

Reactant 1

HCID 674593161-Ethyl-3,3-dimethyl-5-{[(triphenylmethyl)oxy]methyl}-2-pyrrolidinone

Product 1

HCID 67459874HCID 67459874, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Amberlyst 15® (5.56 g, 26.1 mmol) was washed three times with methanol and then a solution of 1-ethyl-3,3-dimethyl-5-{[(triphenylmethyl)oxy]methyl}-2-pyrrolidinone (1.08 g, 2.61 mmol) in methanol (50 ml) was added. The mixture was left to stand for 4 days at room temperature and then the resin was removed by filtration (washing with methanol). The combined methanol fractions were concentrated to give a crude oil (1.62 g) which was purified by automated flash silica-gel column chromatography (Biotage SP4), eluting with a 0-100% gradient of ethyl acetate in hexane, to give pure 1-ethyl-5-(hydroxymethyl)-3,3-dimethyl-2-pyrrolidinone (0.376 g) as an oil that solidified on standing.

Workup

  1. washAmberlyst 15® (5.56 g, 26.1 mmol) was washed three times with methanol
  2. waitThe mixture was left
  3. customthe resin was removed by filtration (washing with methanol)
  4. concentrationThe combined methanol fractions were concentrated
  5. customto give a crude oil (1.62 g) which
  6. customwas purified by automated flash silica-gel column chromatography (Biotage SP4)
  7. washeluting with a 0-100% gradient of ethyl acetate in hexane

Sources & evidence

ORD record
ord-376124b20cf44ab0b1b45375cf83908b
Source dataset
uspto-grants-2011_11
Patent number
US08048907B2

Reaction notes

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