Lithium borohydride → HCID 89487374, compound

HRID 711408Notes

Reaction equation

HRID 711408 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.[Li+].[BH4-]>C1COCC1>[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

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 89493860HCID 89493860, compound

Product 1

HCID 89487374HCID 89487374, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a two necked flask cooled in an ice bath and under argon atmosphere, dimethyl(2S)-2-(1H-pyrrol-1-yl)butanedioate (19 mmol, 4.0 g) was dissolved in 10 ml of dry THF. LiBH4 (57 mmol 1.14 g) was added portionwise and the reaction was stirred for 6 hours at 0° C. When the reaction was completed, it was quenched by addition of 2M HCl and Ethyl Acetate (30 ml). The aqueous layer was extracted with ethyl acetate 2 times and the combined organic layers were dried, filtered and evaporated. The crude residue was purified by chromatography on silica gel (eluent: DCM/MeOH:95/5) to give the product as a colourless oil (2.8 g, 95% yield, e.e. %=97.5).

Workup

  1. temperatureIn a two necked flask cooled in an ice bath and under argon atmosphere
  2. customit was quenched by addition of 2M HCl and Ethyl Acetate (30 ml)
  3. extractionThe aqueous layer was extracted with ethyl acetate 2 times
  4. customthe combined organic layers were dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude residue was purified by chromatography on silica gel (eluent: DCM/MeOH:95/5)

Sources & evidence

ORD record
ord-eedfa44b2b60433a97ee53ceda56f677
Source dataset
uspto-grants-2015_11
Patent number
US09181258B2

Reaction notes

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