Ethyl Acetate → HCID 10867408, compound

HRID 634429Notes

Reaction equation

HRID 634429 reaction equation
[CH3:1][NH:2][CH2:3][C:4]#[CH:5].[CH2:6]([O:13][C:14](ON1C(=O)CCC1=O)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CCCCCCC.CCOC(C)=O>C1COCC1.C([O-])(O)=O.[Na+]>[CH3:1][N:2]([CH2:3][C:4]#[CH:5])[C:14](=[O:15])[O:13][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 8900HeptaneHCID 83172Benzyl succinimido carbonateHCID 96160N-methylpropyn-2-ylamine

Product 1

HCID 10867408HCID 10867408, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of N-methylprop-2-yn-1-amine (3.05 ml, 36.2 mmol) in THF (50 ml) and NaHCO3 sat. aqueous solution (50.0 ml), N-(benzyloxycarbonyloxy)succinimide (11.31 ml, 39.8 mmol) was added and the reaction was stirred overnight. Then, organic layers were extracted with ethyl acetate (2×100 mL). Organic phases were collected, dried, filtered and solvent was removed under reduced pressure. The product was purified by Biotage Si 10 g with a gradient of heptane and EtOAc affording the title compound (5 g, 24.60 mmol, 68.0% yield) as a colorless oil.

Workup

  1. extractionThen, organic layers were extracted with ethyl acetate (2×100 mL)
  2. customOrganic phases were collected
  3. customdried
  4. filtrationfiltered
  5. customsolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-59c64b3e00eb4cc28b4a845dcff406dd
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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