Lithium → (S)-Cyclopropanecarboxylic acid [1-(4-formyl-phenyl)-ethyl]-amide

HRID 523988Notes

Reaction equation

HRID 523988 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([NH:12][C:13]([CH:15]2[CH2:17][CH2:16]2)=[O:14])[CH3:11])=[CH:6][CH:5]=1.[Li]>C1COCC1>[CH:3]([C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([NH:12][C:13]([CH:15]2[CH2:17][CH2:16]2)=[O:14])[CH3:11])=[CH:6][CH:5]=1)=[O:2]

Participants

4

Reactant 2

HCID 3028194LithiumHCID 1189390784-[1-(S)-(cyclopropanecarbonyl-amino)-ethyl]-benzoic acid methyl ester

Product 1

HCID 118940157(S)-Cyclopropanecarboxylic acid [1-(4-formyl-phenyl)-ethyl]-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To 1.95 g (7.89 mmol) 4-[1-(S)-(cyclopropanecarbonyl-amino)-ethyl]-benzoic acid methyl ester in 20 mL THF are added slowly 685 mg (31.6 mmol) lithium borhydride and stirred at 50° C. over night. The reaction is quenched by the addition of a sat. aq. NaHCO3-solution and extracted three times with EtOAc. The organic layers are combined, dried over MgSO4, filtered and the solvent is removed in vacuo.

Workup

  1. customThe reaction is quenched by the addition of a sat. aq. NaHCO3-solution
  2. extractionextracted three times with EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-ba9ec364d08c4b649b03879b4f4defb3
Source dataset
uspto-grants-2016_05
Patent number
US09340510B2

Reaction notes

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