HCID 12194348, 화합물 → HCID 70269233, 화합물

HRID 1504393노트

반응식

HRID 1504393 반응식
[C@@H:1]12[O:7][C@@H:4]([CH:5]=[CH:6]1)[CH2:3][C@H:2]2[C:8]([O:10][CH2:11][CH3:12])=[O:9]>[Pd].C(O)C>[C@@H:1]12[O:7][C@@H:4]([CH2:5][CH2:6]1)[CH2:3][C@H:2]2[C:8]([O:10][CH2:11][CH3:12])=[O:9]

참가 물질

4

반응물 1

HCID 12194348HCID 12194348, 화합물

생성물 1

HCID 70269233HCID 70269233, 화합물수율 92%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A flask was charged with (1R,2R,4R)-ethyl 7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylate (3.91 g, 23.25 mmol) and ethanol (35 mL). The solution was degassed with nitrogen for 5 minutes, then palladium on carbon (5 wt. % wet) (1.0 g, 0.470 mmol) was added portionwise. The flask was evacuated and backfilled three times with nitrogen, then evacuated and backfilled with hydrogen (balloon). The reaction was stirred overnight at room temperature. The reaction was filtered through a plug of Celite and washed several times with ethanol, making sure to keep the catalyst wet with solvent (a layer of sand was added after the first wash). The filtrate was concentrated to afford (1R,2R,4S)-ethyl 7-oxabicyclo[2.2.1]heptane-2-carboxylate (3.63 g, 21.33 mmol, 92% yield). 1H NMR (400 MHz, CHLOROFORM-d) S=4.82 (d, J=5.0 Hz, 1H), 4.72 (t, J=5.0 Hz, 1H), 4.66 (t, J=5.0 Hz, 1H), 4.63-4.59 (m, 1H), 4.22-4.10 (m, 3H), 3.08-2.97 (m, 1H), 2.59 (dd, J=4.9, 9.1 Hz, 1H), 2.14 (dtd, J=2.6, 5.0, 12.3 Hz, 1H), 1.95-1.87 (m, 1H), 1.83-1.63 (m, 4H), 1.62-1.41 (m, 3H), 1.34-1.21 (m, 4H)

후처리

  1. customThe solution was degassed with nitrogen for 5 minutes
  2. customThe flask was evacuated
  3. customevacuated
  4. filtrationThe reaction was filtered through a plug of Celite
  5. washwashed several times with ethanol
  6. additionwas added after the
  7. washfirst wash)
  8. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-f871a53b3d654a0e8ab1e68741f700bd
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212182B2

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