Ethyl Acetate → HCID 66803790, compound

HRID 1844001Notes

Reaction equation

HRID 1844001 reaction equation
[BH4-].[Na+].[C:3]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:10]=1[CH2:11][C:12](OC)=[O:13])#[N:4].C(OCC)(=O)C>C(O)C.CCCCCC>[OH:13][CH2:12][CH2:11][C:10]1[C:5]([C:3]#[N:4])=[CH:6][N:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 53419517Methyl 2-(3-cyanopyridin-4-YL)acetate

Product 1

HCID 66803790HCID 66803790, compoundYield 22.42%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

NaBH4 (228 mg, 6.023 mmol) was added portion wise over a period of 20 minutes to a solution of methyl 2-(3-cyanopyridin-4-yl)acetate (I-65a: 530 mg, 3.011 mmol) in ethanol (6 mL) at 0° C. and the resulting reaction mass was stirred at 0° C. for 4 hours. The reaction was monitored by TLC (50% ethyl acetate in hexane). The reaction mass was quenched with saturated NH4Cl solution and extracted using ethyl acetate. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (2% methanol in DCM) afforded 100 mg of the product (22.42% yield).

Workup

  1. customthe resulting reaction mass
  2. customThe reaction mass was quenched with saturated NH4Cl solution
  3. extractionextracted
  4. washThe organic layer was washed with water, brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto afford the crude product
  8. customPurification by column chromatography on silica gel (2% methanol in DCM)

Sources & evidence

ORD record
ord-67014bf1087648f1b7d9ef2fe1900c37
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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