(2S)-1-Methyl-2-pyrrolidinemethanol → HCID 67196435, compound

HRID 551381Notes

Reaction equation

HRID 551381 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][OH:8].C[O:10][C:11](=O)[C:12]([OH:23])([C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)[C:13]1[S:14][CH:15]=[CH:16][CH:17]=1.[Na]>C1(C)C=CC=CC=1.C(OCC)C>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][O:8][C:11](=[O:10])[C:12]([OH:23])([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)[C:18]1[S:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 643492(2S)-1-Methyl-2-pyrrolidinemethanolHCID 5360545Sodium2×HCID 11414137Methyl alpha-hydroxy-alpha-2-thienyl-2-thiopheneacetate

Product 1

HCID 67196435HCID 67196435, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of molecular sieve 4A, ((S)-1-Methyl-pyrrolidin-2-yl)-methanol (3.71 g, 31.2 mmol) and Hydroxy-di-thiophen-2-yl-acetic acid methyl ester (3.96 g, 15.6 mmol) in toluene (40 ml) is added sodium (65 mg) and the suspension is heated under stirring to 80° C. for 3.5 hours. Additional sodium (65 mg) is then added and the reaction mixture stirred at 80° C. for 16 hours. The reaction mixture is cooled to room temperature, diluted with diethylether (100 ml) and extracted with HCl 1 M (2×100 ml). The combined acidic aqueous layers are washed with diethylether (50 ml) and basified with sodium hydroxide 4 M whilst cooling in ice. The solution is then extracted with ethylacetate and diethylether. The combined organic layers are dried over magnesium sulphate, filtered and evaporated to dryness to give the title product.

Workup

  1. temperaturethe suspension is heated
  2. stirringthe reaction mixture stirred at 80° C. for 16 hours
  3. temperatureThe reaction mixture is cooled to room temperature
  4. extractionextracted with HCl 1 M (2×100 ml)
  5. washThe combined acidic aqueous layers are washed with diethylether (50 ml)
  6. temperaturewhilst cooling in ice
  7. extractionThe solution is then extracted with ethylacetate and diethylether
  8. dry with materialThe combined organic layers are dried over magnesium sulphate
  9. filtrationfiltered
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-a3364f35d21941e78e0ba65de029c9a8
Source dataset
uspto-grants-2011_05
Patent number
US07947730B2

Reaction notes

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