Hydrochloric Acid → HCID 89487374, compound

HRID 711407Notes

Reaction equation

HRID 711407 reaction equation
[N:1]1([C@@H:6]([CH2:11][C:12](OC)=[O:13])[C:7](OC)=[O:8])[CH:5]=[CH:4][CH:3]=[CH:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl.O>C1COCC1.CCOC(C)=O>[N:1]1([C@@H:6]([CH2:11][CH2:12][OH:13])[CH2:7][OH:8])[CH:5]=[CH:4][CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 89493860HCID 89493860, compound

Product 1

HCID 89487374HCID 89487374, compoundYield 63.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a two necked flask cooled in an ice bath and under argon atmosphere, dimethyl(2S)-2-(1H-pyrrol-1-yl)butanedioate (20.3 mmol, 4.3 g) was dissolved in 50 ml of dry THF. LiAlH4 (42 ml, 1 M in THF) was cautiously added and the reaction was let warm up at room temperature. When the reaction was completed, it was cooled again to 0° C. and acidified with 2M HCl. Water and AcOEt were added to the quenched reaction and the organic layer was extracted with brine. The crude residue was purified by chromatography on silica gel (eluent: DCM/MeOH:95/5) to give the product as a colourless oil (2.0 g, 63% yield).

Workup

  1. temperatureIn a two necked flask cooled in an ice bath and under argon atmosphere
  2. temperatureit was cooled again to 0° C.
  3. extractionthe organic layer was extracted with brine
  4. customThe crude residue was purified by chromatography on silica gel (eluent: DCM/MeOH:95/5)

Sources & evidence

ORD record
ord-6e90bfb4467c4301a3fd6617ce316398
Source dataset
uspto-grants-2015_11
Patent number
US09181258B2

Reaction notes

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