Tetrahydrofuran → HCID 86709725, compound

HRID 2285429Notes

Reaction equation

HRID 2285429 reaction equation
[Cl:1][C:2]([Cl:13])([Cl:12])[C@H:3]1[N:7]2[CH2:8][CH2:9][CH2:10][C@@H:6]2[C:5](=[O:11])[O:4]1.[Li+].CC([N-]C(C)C)C.CCCCCC.C1C[O:31][CH2:30]C1>>[O:11]=[C:5]1[O:4][C@@H:3]([C:2]([Cl:1])([Cl:12])[Cl:13])[N:7]2[CH2:8][CH2:9][CH2:10][C@:6]12[CH:30]=[O:31]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8058HexaneHCID 2724682Lithium diisopropylamideHCID 45158923(3S,7aR)-Tetrahydro-3-(trichloromethyl)-1H,3H-pyrrolo[1,2-c]oxazol-1-one

Product 1

HCID 86709725HCID 86709725, compoundYield 37%

Conditions

Temperature
-78 °C

Procedure

To reactant 155a (4.8 g, 19.8 mmol) suspended in anhydrous THF (100 mL) at −78° C., was added 2.0 M LDA in Hexane (14.9 mL, 29.7 mmol) over 20 min period. The mixture was stirred at −78° C. for 45 min, then let it warm up to 0° C. over 3 hour. Reaction was monitored by TLC. After completion, the reaction was quenched by adding aq. 10% citric acid slowly. It was extracted with EtOAc twice, washed with brine. The organic layer was dried through (Na2SO4), and concentrated; the residue was purified by CombiFlash using EtOAC/Hexane as eluents to give (3S,7aS)-1-oxo-3-(trichloromethyl)hexahydropyrrolo-[1,2-c]oxazole-7a-carbaldehyde 155b 1.99 g, 37%.

Workup

  1. temperaturewarm up to 0° C. over 3 hour
  2. customReaction
  3. customAfter completion, the reaction was quenched
  4. additionby adding aq. 10% citric acid slowly
  5. extractionIt was extracted with EtOAc twice
  6. washwashed with brine
  7. dry with materialThe organic layer was dried through (Na2SO4)
  8. concentrationconcentrated
  9. customthe residue was purified by CombiFlash

Sources & evidence

ORD record
ord-865e9988903c42f78bda88282f944aae
Source dataset
uspto-grants-2015_09
Patent number
US09145441B2

Reaction notes

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