Ethyl Acetate → HCID 178454125, compound

HRID 577740Notes

Reaction equation

HRID 577740 reaction equation
[O:1]=[C:2]1[CH2:5][CH:4]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:3]1.[Li].CCOC(C)=O>C1COCC1>[C:9]([O:8][C:7](=[O:13])[NH:6][C@H:4]1[CH2:5][C@@H:2]([OH:1])[CH2:3]1)([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 8857Ethyl Acetate2×HCID 3028194LithiumHCID 23374584tert-Butyl 3-oxocyclobutylcarbamate

Product 1

HCID 178454125HCID 178454125, compoundYield 613.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl (3-oxocyclobutyl)carbamate (100 g, 54 mmol) in THF (2000 mL) at −72° C. was added dropwise a solution of lithium trisec-butylhidridoborate (648 mL, 1 M) in THF over 1.5 hrs. The resulting solution was allowed to warm up to rt and stirred for another 1 hr. TLC (petroleum ether: EtOAc=2:1) showed that the starting material was consumed completely. The reaction was quenched with NH4Cl aqueous. Water (1000 mL) and EtOAc (2000 mL) were added to the mixture. The organic layer was separated, dried over MgSO4 and concentrated to give crude material, which was purified by column chromatography with petroleum ether: EtOAc from 10:1 to 1:2 to afford the title compound (62 g, 61% yield) as a white solid.

Workup

  1. customwas consumed completely
  2. customThe reaction was quenched with NH4Cl aqueous
  3. additionWater (1000 mL) and EtOAc (2000 mL) were added to the mixture
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give crude material, which
  8. customwas purified by column chromatography with petroleum ether

Sources & evidence

ORD record
ord-e2636a274d834bffa6e30f06fe521511
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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