Methanol → Methyl 1-benzyl-4-methylpyrrolidine-3-carboxylate

HRID 1875333Notes

Reaction equation

HRID 1875333 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([CH3:13])[CH:10]([C:14]([OH:16])=[O:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:21]O>>[CH2:1]([N:8]1[CH2:12][CH:11]([CH3:13])[CH:10]([C:14]([O:16][CH3:21])=[O:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 50457831-Benzyl-4-methylpyrrolidine-3-carboxylic acid

Product 1

HCID 3638244Methyl 1-benzyl-4-methylpyrrolidine-3-carboxylate

Procedure

1.3 g (4.9 mmol) (3RS,4RS)-1-benzyl-4-methyl-pyrrolidine-3-carboxylic acid (as hydrochloride salt) are dissolved in 10 ml of methanol and combined with 0.6 ml (8.5 mmol) thionyl chloride while cooling with an ice bath. The ice bath is removed and the mixture is refluxed for three hours. Then the mixture is evaporated down i. vac. and combined with 1N sodium hydroxide solution. The aqueous phase is extracted three times with ethyl acetate. The combined organic phases are dried on sodium sulphate, filtered and evaporated down i. vac.

Workup

  1. temperaturewhile cooling with an ice bath
  2. customThe ice bath is removed
  3. temperaturethe mixture is refluxed for three hours
  4. customThen the mixture is evaporated down i
  5. extractionThe aqueous phase is extracted three times with ethyl acetate
  6. customThe combined organic phases are dried on sodium sulphate
  7. filtrationfiltered
  8. customevaporated down i

Sources & evidence

ORD record
ord-410fbd118ff542558046a7703dec87aa
Source dataset
uspto-grants-2012_11
Patent number
US08309542B2

Reaction notes

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